Acetic Acid → 2-{1-[4-(6-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)-benzyl]-piperidin-4-yl}-3H-benzimidazol-5-carbonitrile

HRID 1851264노트

반응식

HRID 1851264 반응식
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[NH:9][C:10]3[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:26]1([C:32]2[C:33]([C:41]3[CH:48]=[CH:47][C:44]([CH:45]=O)=[CH:43][CH:42]=3)=[N:34][C:35]3[N:36]([N:38]=[CH:39][CH:40]=3)[CH:37]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.ClCCl.CN(C=O)C>[C:26]1([C:32]2[C:33]([C:41]3[CH:42]=[CH:43][C:44]([CH2:45][N:2]4[CH2:3][CH2:4][CH:5]([C:8]5[NH:9][C:10]6[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[CH:13][C:11]=6[N:12]=5)[CH2:6][CH2:7]4)=[CH:47][CH:48]=3)=[N:34][C:35]3[N:36]([N:38]=[CH:39][CH:40]=3)[CH:37]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

9

반응물 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydride2회HCID 687529322-Piperidin-4-yl-1h-benzoimidazole-5-carbonitrile hydrochloride saltHCID 866306654-(6-Phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

생성물 1

HCID 687516862-{1-[4-(6-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)-benzyl]-piperidin-4-yl}-3H-benzimidazol-5-carbonitrile수율 32.2%

시약·촉매·용매 3

HCID 887Methanol용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

265 mg (1 mmol) 2-piperidine-4-yl-3H-benzimidazole-5-carbonitrile hydrochloride salt was dissolved in 5 mL methanol. 204 mg (2 mmol) triethylamine, 250 mg (0.84 mmol) 4-(6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde, 5 mL DMF, 12.5 mL dichloromethane and 131 mg (2.2 mmol) acetic acid were added and after 30 minutes stirring 355 mg (1.68 mmol) NaBH(OAc)3 was added. Additional NaBH(OAc)3 has been added after one, two, three and four hours (two equivalents each) and the reaction mixture has been stirred overnight at room temperature. Usual work-up and purification as described in previous experiments yields 138 mg of the desired material.

후처리

  1. additionwas added
  2. customUsual work-up and purification

출처 및 근거

ORD 기록
ord-743b974d833e43ab8dfec5863ae02371
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957064B2

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