Dihydroxybenzylamine → 5-[3-({[(3,4-dihydroxyphenyl)methyl]amino}methyl)phenyl]-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

HRID 1806235

반응식

HRID 1806235 반응식
[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].[NH2:32][CH2:33][C:34]1[CH:35]=[C:36]([OH:41])[C:37]([OH:40])=[CH:38][CH:39]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[OH:41][C:36]1[CH:35]=[C:34]([CH2:33][NH:32][CH2:27][C:23]2[CH:22]=[C:21]([C:18]3[CH:19]=[C:20]4[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=3)[NH:14][CH:13]=[C:12]4[CH:9]3[CH2:10][CH2:11][N:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH2:7][CH2:8]3)[CH:26]=[CH:25][CH:24]=2)[CH:39]=[CH:38][C:37]=1[OH:40]

참가 물질

5

반응물 3

HCID 91623DihydroxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 577328043-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide

생성물 1

HCID 160382035-[3-({[(3,4-dihydroxyphenyl)methyl]amino}methyl)phenyl]-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide수율 15.1%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide (50 mg, 0.114 mmol) in dichloroethane (2 mL) was added 4-(aminomethyl)-1,2-benzenediol (12.1 mg, 0.087 mmol). The reaction solution was stirred at ambient temperature for 10 min prior to addition of NaBH(OAc)3 (58 mg, 0.261 mmol). The resulting mixture was shaken overnight at ambient temperature after which time the solvent was removed under reduced pressure. The crude product was purified by reverse phase HPLC (water/CH3CN, 0.1% TFA 10-90%) to give the title compound (7.4 mg, 12%).

후처리

  1. stirringThe resulting mixture was shaken overnight at ambient temperature after which time the solvent
  2. customwas removed under reduced pressure
  3. customThe crude product was purified by reverse phase HPLC (water/CH3CN, 0.1% TFA 10-90%)

출처 및 근거

ORD 기록
ord-16a06a40570c43ab95fa819c4bcc2391
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354406B2

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