Benzaldehyde → HCID 10348365, compound

HRID 585041Notes

Reaction equation

HRID 585041 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=2[NH:21][C:22]([C:24]2[CH:32]=[C:31]([Cl:33])[C:30]([Cl:34])=[CH:29][C:25]=2[C:26]([OH:28])=[O:27])=[O:23])=[CH:6][CH:5]=1.[CH:35](=O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.CO>[CH2:35]([NH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:13][C:12]=2[NH:21][C:22]([C:24]2[CH:32]=[C:31]([Cl:33])[C:30]([Cl:34])=[CH:29][C:25]=2[C:26]([OH:28])=[O:27])=[O:23])=[CH:8][CH:9]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 9871811HCID 9871811, compound

Product 1

HCID 10348365HCID 10348365, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

In a small round bottom flask equipped with a stirbar, 2-({[2-{[4-(aminomethyl)phenyl]amino}-5-(trifluoromethyl)phenyl]amino}carbonyl)-4,5-dichlorobenzoic acid hydrochloride (0.2 mmol, 107 mg) is combined with benzaldehyde (0.96 mmol, 102 mg) and diluted with 1 mL acetic acid and 4 mL methanol. After 15 minutes, sodium cyanoborohydride (3.5 mmol, 0.24 mL) is added portionwise. After 20 hours, the reaction is stopped. The reaction mixture is made basic with 5N NaOH and extracted three times with ethyl acetate. The organics are combined and washed with brine then dried over MgSO4. After concentration the crude oil is purified by column chromatography (100% EtOAc) to give a white solid in low yield. 1H NMR (400 MHz, DMSO-d6): □ 10.39 (s, 1H), 7.98 (m, 1H), 7.80 (s, 1H), 7.66 (s, 1H), 7.43, (m, 14H), 4.12 (m, 4H). ESI+ for C29H22Cl2F3N3O3 m/z 588 M+.

Workup

  1. waitAfter 20 hours
  2. extractionextracted three times with ethyl acetate
  3. washwashed with brine
  4. dry with materialthen dried over MgSO4
  5. concentrationAfter concentration the crude oil
  6. customis purified by column chromatography (100% EtOAc)
  7. customto give a white solid in low yield

Sources & evidence

ORD record
ord-a2eb190a36a44c818136d79c368fcc74
Source dataset
uspto-grants-2005_08
Patent number
US06930106B2

Reaction notes

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