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

HRID 1851269
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HRID 1851269 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 3

HCID 5049666Sodium triacetoxyborohydride2회HCID 687529342-Piperidine-4-yl-6-trifluoromethyl-1h-benzimidazole hydrochloride salt2회HCID 866306654-(6-Phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

생성물 1

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

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-5f4e87defabc4e5fa29acd39a04d847d
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08957064B2

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