Sodium triacetoxyborohydride → 6-phenyl-5-{4-[4-(6-trifluoromethyl-1H-benzimidazol-2-yl)piperidin-1-ylmethyl]-phenyl}-pyrazolo[1,5-a]pyrimidine

HRID 1851269Notes

Reaction equation

HRID 1851269 reaction equation
[C:1]1([C:7]2[C:8]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)=[N:9][C:10]3[N:11]([N:13]=[CH:14][CH:15]=3)[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH:25]1[CH2:30][CH2:29][CH:28]([C:31]2[NH:35][C:34]3[CH:36]=[C:37]([C:40]([F:43])([F:42])[F:41])[CH:38]=[CH:39][C:33]=3[N:32]=2)[CH2:27][CH2:26]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:1]1([C:7]2[C:8]([C:16]3[CH:23]=[CH:22][C:19]([CH2:20][N:25]4[CH2:30][CH2:29][CH:28]([C:31]5[NH:35][C:34]6[CH:36]=[C:37]([C:40]([F:43])([F:42])[F:41])[CH:38]=[CH:39][C:33]=6[N:32]=5)[CH2:27][CH2:26]4)=[CH:18][CH:17]=3)=[N:9][C:10]3[N:11]([N:13]=[CH:14][CH:15]=3)[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydride2×HCID 687529342-Piperidine-4-yl-6-trifluoromethyl-1h-benzimidazole hydrochloride salt2×HCID 866306654-(6-Phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

Product 1

HCID 687546116-phenyl-5-{4-[4-(6-trifluoromethyl-1H-benzimidazol-2-yl)piperidin-1-ylmethyl]-phenyl}-pyrazolo[1,5-a]pyrimidineYield 44.8%

Procedure

250 mg (0.84 mmol) 4-(6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde and 308 mg (1 mmol) 2-piperidine-4-yl-6-trifluoromethyl-1H-benzimidazole hydrochloride salt were treated as previously described. Additional NaBH(OAc)3 has been added after one, two and three hours (two equivalents each). After a further hour stirring at room temperature additional 31 mg 2-piperidine-4-yl-6-trifluoromethyl-1H-benzimidazole hydrochloride salt and two equivalents NaBH(OAc)3 were added. After stirring overnight and two further additions of NaBH(OAc)3 the solvents were evaporated. Workup and purification yields 208 mg of the desired compound.

Workup

  1. additionwere added
  2. customtwo further additions of NaBH(OAc)3 the solvents were evaporated
  3. customWorkup and purification

Sources & evidence

ORD record
ord-5f4e87defabc4e5fa29acd39a04d847d
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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