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

HRID 1851270노트

반응식

HRID 1851270 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.[F:25][C:26]1[CH:27]=[CH:28][C:29]2[N:33]=[C:32]([CH:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[NH:31][C:30]=2[CH:40]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[F:25][C:26]1[CH:27]=[CH:28][C:29]2[N:33]=[C:32]([CH:34]3[CH2:35][CH2:36][N:37]([CH2:20][C:19]4[CH:22]=[CH:23][C:16]([C:8]5[C:7]([C:1]6[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=6)=[CH:12][N:11]6[N:13]=[CH:14][CH:15]=[C:10]6[N:9]=5)=[CH:17][CH:18]=4)[CH2:38][CH2:39]3)[NH:31][C:30]=2[CH:40]=1

참가 물질

4

반응물 3

HCID 5049666Sodium triacetoxyborohydride2회HCID 534298905-Fluoro-2-piperidin-4-YL-1H-benzoimidazole hydrochloride2회HCID 866306654-(6-Phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

생성물 1

HCID 687537915-{4-[4-(6-fluoro-1H-benzimidazol-2-yl)-piperidin-1-ylmethyl]-phenyl}-6-phenyl-pyrazolo[1,5-a]pyrimidine수율 59%

실험 절차

250 mg (0.84 mmol) 4-(6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde and 258 mg (1 mmol) 6-fluoro-2-piperidine-4-yl-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 26 mg 6-fluoro-2-piperidine-4-yl-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 249 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-9f6ce07b32ad4e22b8207d12c5c608d0
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957064B2

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