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

HRID 1851264ノート

反応式

HRID 1851264 の反応式
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

参加物

9

反応物 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydride2 回HCID 687529322-Piperidin-4-yl-1h-benzoimidazole-5-carbonitrile hydrochloride saltHCID 866306654-(6-Phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-743b974d833e43ab8dfec5863ae02371
出典データセット
uspto-grants-2015_02
特許番号
US08957064B2

反応ノート

読み込み中…