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

HRID 1851270ノート

反応式

HRID 1851270 の反応式
[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

参加物

4

反応物 3

HCID 5049666Sodium triacetoxyborohydride2 回HCID 534298905-Fluoro-2-piperidin-4-YL-1H-benzoimidazole hydrochloride2 回HCID 866306654-(6-Phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

生成物 1

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

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-9f6ce07b32ad4e22b8207d12c5c608d0
出典データセット
uspto-grants-2015_02
特許番号
US08957064B2

反応ノート

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