Hydrochloric Acid → HCID 57345649, compound

HRID 1889221Notes

Reaction equation

HRID 1889221 reaction equation
[C:1]([C:5]1[CH:30]=[CH:29][C:8]([C:9]([NH:11][C:12](=[O:28])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:27])[CH2:22][CH2:23][CH2:24][CH2:25]Br)=[CH:16][CH:15]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:31]([CH3:33])[CH3:32].O.[ClH:35]>C(Cl)Cl.CC(C)=O.C(OCC)C>[ClH:35].[C:1]([C:5]1[CH:30]=[CH:29][C:8]([C:9]([NH:11][C:12](=[O:28])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:27])[CH2:22][CH2:23][CH2:24][CH2:25][N:31]([CH3:33])[CH3:32])=[CH:16][CH:15]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 962WaterHCID 66838782HCID 66838782, compound

Product 1

HCID 57345649HCID 57345649, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Bromo-compound 29 (123 mg, 0.27 mmol) was stirred in CH2Cl2 (10 mL), 40% aqueous HNMe2 (3 mL) and H2O (7.5 mL) at rt for 20 h. The reaction mixture was diluted with CH2Cl2 (20 mL) and washed with H2O (1×10 mL), 10% aqueous NaOH (1×10 mL), and saturated brine (1×10 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give a cream solid which was dissolved in acetone and treated with 2 M hydrochloric acid in diethyl ether. A white precipitate was obtained and isolated by filtration to give 24 (44 mg, 36%) as a cream powder. 1H NMR (DMSO-d6, 400 MHz) δ 1.31 (s, 9H, (CH3)3), 1.64 (m, 4H, CH2)2), 2.36 (t, 2H, J=6.7 Hz, COCH2), 2.75 (s, 6H, NH(CH3)2), 3.05 (m, 2H, CH2Br), 7.53 (m, 6H, ArH), 7.98 (d, 2H, J=8.6 Hz, ArH), 9.63 (s(br), 1H, NH), 9.98 (s, 1H, NH), 10.82 (s, 1H, NH), 10.93 (s, 1H, NH).

Workup

  1. washwashed with H2O (1×10 mL), 10% aqueous NaOH (1×10 mL), and saturated brine (1×10 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give a cream solid which
  5. customA white precipitate was obtained
  6. customisolated by filtration

Sources & evidence

ORD record
ord-b5d28e7fb6624c1a91c5f9d337d8bd2b
Source dataset
uspto-grants-2013_08
Patent number
US08501991B2

Reaction notes

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