Acetic Acid → HCID 57863420, compound

HRID 1446759Notes

Reaction equation

HRID 1446759 reaction equation
[NH2:1][CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][N:16]3[C:19]([C:22]4[CH:27]=[CH:26][C:25]([CH2:28][C:29]([NH:31][C:32]5[CH:36]=[C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])[O:34][N:33]=5)=[O:30])=[CH:24][CH:23]=4)=[CH:20][N:21]=[C:15]3[CH:14]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5].[C:41](O)(=O)[CH3:42].[CH:45](=O)[CH3:46].C([BH3-])#N.[Na+]>CO>[C:37]([C:35]1[O:34][N:33]=[C:32]([NH:31][C:29](=[O:30])[CH2:28][C:25]2[CH:26]=[CH:27][C:22]([C:19]3[N:16]4[CH:17]=[CH:18][C:13]([C:10]5[CH:11]=[CH:12][C:7]([S:4]([CH2:3][CH2:2][N:1]([CH2:41][CH3:42])[CH2:45][CH3:46])(=[O:5])=[O:6])=[CH:8][CH:9]=5)=[CH:14][C:15]4=[N:21][CH:20]=3)=[CH:23][CH:24]=2)[CH:36]=1)([CH3:40])([CH3:39])[CH3:38]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68542292HCID 68542292, compound

Product 1

HCID 57863420HCID 57863420, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 2-(4-{7-[4-(2-Amino-ethanesulfonyl)-phenyl]-imidazo[1,2-a]pyridin-3-yl}-phenyl)-N-(5-tert-butyl-isoxazol-3-yl)-acetamide (0.87 g, 1.38 mmol) with acetic acid (1 mL), methanol (20 mL) and acetaldehyde (0.152 g, 3.45 mmol) at ambient temperature under nitrogen for 10 minutes. Add sodium cyanoborohydride at ambient temperature. The reaction is complete within 3 hours. Evaporate under vacuum, re-dissolved in methanol and dichloromethane and load onto an SCX column. Wash the column with dichloromethane (50 mL) and methanol (50 mL) and elute with methanolic ammonia. Chromatography on silica (0→2→4→5%) methanol and dichloromethane gives the title compound (21.0 mg). MS(ES), m/z 614 (M+1).

Workup

  1. customat ambient temperature
  2. customEvaporate under vacuum
  3. dissolutionre-dissolved in methanol
  4. washWash the column with dichloromethane (50 mL) and methanol (50 mL)
  5. washelute with methanolic ammonia

Sources & evidence

ORD record
ord-c2e1b9f3c2fa45f2ab9498b140c9a3dd
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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