Acetic Acid → HCID 68386507, compound

HRID 1051176Notes

Reaction equation

HRID 1051176 reaction equation
[NH2:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([C:11]3[CH:22]=[CH:21][C:14]([C:15]([NH:17][CH:18]4[CH2:20][CH2:19]4)=[O:16])=[C:13]([CH3:23])[CH:12]=3)[C:6]=2[CH:5]=[C:4]([Br:24])[CH:3]=1.[F:25][C:26]([F:31])([F:30])[CH2:27][CH:28]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.C(Cl)Cl.O>[Br:24][C:4]1[CH:3]=[C:2]([NH:1][CH2:28][CH2:27][C:26]([F:31])([F:30])[F:25])[C:10]2[N:9]=[CH:8][N:7]([C:11]3[CH:22]=[CH:21][C:14]([C:15]([NH:17][CH:18]4[CH2:19][CH2:20]4)=[O:16])=[C:13]([CH3:23])[CH:12]=3)[C:6]=2[CH:5]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 680283,3,3-TrifluoropropanalHCID 5049666Sodium triacetoxyborohydrideHCID 68386499HCID 68386499, compound

Product 1

HCID 68386507HCID 68386507, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(4-amino-6-bromo-1H-benzimidazol-1-yl)-N-cyclopropyl-2-methylbenzamide (5.00 g, 12.98 mmol) in DCE at rt was added 3,3,3-trifluoropropanal (4.36 g, 38.93 mmol, 3 eq), sodium triacetoxy borohydride (13.75 g, 64.89 mmol, 5 eq) and acetic acid (14.9 mL, 259.56 mmol, 20 eq) and the mixture was stirred for overnight. Water and DCM was added, and the organic phase was separated and washed with water After addition of DCM, the organic phase was washed with water and evaporated to yield 4-{6-bromo-4-[(3,3,3-trifluoropropyl)amino]-1H-benzimidazol-1-yl}-N-cyclopropyl-2-methylbenzamide (50%).

Workup

  1. customthe organic phase was separated
  2. washwashed with water
  3. additionAfter addition of DCM
  4. washthe organic phase was washed with water
  5. customevaporated

Sources & evidence

ORD record
ord-9b6871f9099947cf9828ae19dd8d783c
Source dataset
uspto-grants-2016_07
Patent number
US09388140B2

Reaction notes

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