Acetic Acid → HCID 69662766, compound

HRID 1792260Notes

Reaction equation

HRID 1792260 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[C:17]2[N:16]3[C:11]([C:12]([C:18]4[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=4[CH3:26])=[CH:13][CH:14]=[CH:15]3)=[CH:10][C:9]=2[N:8]=[C:7]([CH3:27])[N:6]=1.[C:28]1(=O)[CH2:32][CH2:31][CH2:30][CH2:29]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(Cl)Cl>[CH:28]1([NH:1][CH2:2][CH2:3][NH:4][C:5]2[C:17]3[N:16]4[C:11]([C:12]([C:18]5[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=5[CH3:26])=[CH:13][CH:14]=[CH:15]4)=[CH:10][C:9]=3[N:8]=[C:7]([CH3:27])[N:6]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 5049666Sodium triacetoxyborohydrideHCID 69662159HCID 69662159, compound

Product 1

HCID 69662766HCID 69662766, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Treat a solution of (2-aminoethyl)[2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indolizin-4-yl]amine (0.07 g, 0.19 mmol), cyclopentanone (0.02 mL, 0.19 mmol) and acetic acid (0.01 mL, 0.19 mmol) in dry dichloroethane (3 mL) with sodium triacetoxyborohydride (0.06 g, 0.27 mmol) and stir at ambient temperature for 14 h. Dilute the resulting mixture with CH2Cl2 (20 mL) and wash with saturated aq NaCl (50 mL). Dry the organic portion over Na2SO4, filter, and concentrate under reduced pressure. Purify by preparative TLC (10% MeOH in CH2Cl2 with 0.5% ammonium hydroxide) to obtain the title compound as a yellow solid.

Workup

  1. washwash with saturated aq NaCl (50 mL)
  2. dry with materialDry the organic portion over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure
  5. customPurify by preparative TLC (10% MeOH in CH2Cl2 with 0.5% ammonium hydroxide)

Sources & evidence

ORD record
ord-b280c7e4cd58488ab2913354e1aa71a7
Source dataset
uspto-grants-2006_07
Patent number
US07074929B2

Reaction notes

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