Sodium → HCID 178448644, compound

HRID 733235Notes

Reaction equation

HRID 733235 reaction equation
[Na].[Cl-].[NH2:3][C:4]([NH2:6])=[NH2+:5].[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH2:17][C:18](OCC)=[O:19])[N:12]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:11]2=[O:27].[Br:28][C:29]1[CH:37]=[C:36]2[C:32]([C:33](=[O:48])[N:34]([CH2:44][CH:45]([CH3:47])[CH3:46])[CH:35]2[CH2:38][C:39](OCC)=[O:40])=[CH:31][CH:30]=1>C(O)C.O.C(OCC)C>[Br:28][C:29]1[CH:37]=[C:36]2[C:32]([C:33](=[O:48])[N:34]([CH2:44][CH:45]([CH3:46])[CH3:47])[CH:35]2[CH2:38][C:39]([NH:5][C:4]([NH2:6])=[NH:3])=[O:40])=[CH:31][CH:30]=1.[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH2:17][C:18]([NH:5][C:4]([NH2:6])=[NH:3])=[O:19])[N:12]([CH2:23][CH:24]([CH3:25])[CH3:26])[C:11]2=[O:27]

Participants

9

Reactant 4

HCID 5360545SodiumHCID 5460839Carbamimidoylazanium ChlorideHCID 69714493HCID 69714493, compoundHCID 86591364HCID 86591364, compound

Product 2

HCID 178448644HCID 178448644, compoundHCID 178448645HCID 178448645, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

N-[(5-Bromo-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine and N-[(6-bromo-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine are prepared as described in Example 9, starting with 30 cm3 of absolute ethanol, 0.36 g of sodium, 1.5 g of guanidinium chloride and 3.7 g of ethyl (5-bromo-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate and ethyl (6-bromo-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate in 20 cm3 of absolute ethanol. The reaction mixture is stirred at a temperature in the region of 20° C. for 16 hours and is then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is taken up in a mixture of 100 cm3 of water and 200 cm3 of ethyl acetate. The organic phase is washed with 100 cm3 of water and then with 150 cm3 of saturated sodium chloride solution. This organic phase is dried over magnesium sulfate and concentrated under reduced pressure (2 kPa) at a temperature in the region of 40° C. A white solid is thus obtained, which is then taken up again and stirred in a mixture of 15 cm3 of water and 50 cm3 of diethyl ether for 1.5 hours at a temperature in the region of 20° C. The white solid thus obtained is filtered off, washed with twice 50 cm3 of diethyl ether and dried in a desiccator under reduced pressure (2 Pa) at a temperature in the region of 35° C. 0.92 g of N-[(5-bromo-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine and N-[(6-bromo-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine are thus obtained in the form of a white powder. (Analysis: C15 H19 Br N4 O2, % calculated C, 49.06; H, 5.21; Br, 21.76; N, 15.26; O, 8.71%. found C, 48.97; H, 5.34; Cl, 14.72; N, 21.52). Mass spectrum: EI: m/e 366 (M+), m/e 279, m/e 86 (base peak).

Workup

  1. concentrationis then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  2. additionThe residue is taken up in a mixture of 100 cm3 of water and 200 cm3 of ethyl acetate
  3. washThe organic phase is washed with 100 cm3 of water
  4. dry with materialThis organic phase is dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure (2 kPa) at a temperature in the region of 40° C
  6. customA white solid is thus obtained
  7. customThe white solid thus obtained
  8. filtrationis filtered off
  9. washwashed with twice 50 cm3 of diethyl ether
  10. customdried in a desiccator under reduced pressure (2 Pa) at a temperature in the region of 35° C

Sources & evidence

ORD record
ord-bd0f7cce3bb442f58c35670aae9112e6
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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