Piperidine → HCID 11990801、化合物

HRID 562032

反応式

HRID 562032 の反応式
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=O)[CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[NH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH2:1]([S:3]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][N:32]5[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]5)[CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:11]1)(=[O:4])=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 577328043-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide

生成物 1

HCID 11990801HCID 11990801、化合物収率 50.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide (15.0 mg, 0.034 mmol) in DCM (2 mL) was added piperidine (4.0 ul, 0.04 mmol). The reaction solution was stirred at ambient temperature for 1 hr prior to addition of NaBH(OAc)3 (23.0 mg, 0.109 mmol). The resulting mixture was stirred overnight at ambient temperature after which time the solvent was removed under reduced pressure. The resulting residue was dissolved in 1.2 mL DMSO and all undissolved solid was filtered off. This DMSO solution of crude product was purified by reverse phase HPLC (H2O/CH3CN, 0.1% TFA 10-90%) to give the title compound (8.8 mg, 50.5%).

後処理

  1. stirringThe resulting mixture was stirred overnight at ambient temperature after which time the solvent
  2. customwas removed under reduced pressure
  3. dissolutionThe resulting residue was dissolved in 1.2 mL DMSO
  4. filtrationall undissolved solid was filtered off
  5. customThis DMSO solution of crude product was purified by reverse phase HPLC (H2O/CH3CN, 0.1% TFA 10-90%)

出典と根拠

ORDレコード
ord-81b5deac3a634227833c68b09c8b8457
出典データセット
uspto-grants-2011_11
特許番号
US08063071B2

関連ノート

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