Methanol → 5-(3-cyano-5-{[(2,2,2-trifluoroethyl)amino]methyl}phenyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide trifluoroacetate

HRID 1806259노트

반응식

HRID 1806259 반응식
[C:1]([C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[C:13]3[C:17](=[C:18]([C:20]([NH2:22])=[O:21])[CH:19]=2)[NH:16][CH:15]=[C:14]3[CH:23]2[CH2:28][CH2:27][N:26]([S:29]([CH2:32][CH3:33])(=[O:31])=[O:30])[CH2:25][CH2:24]2)[CH:6]=[C:7]([CH:9]=O)[CH:8]=1)#[N:2].[F:34][C:35]([F:39])([F:38])[CH2:36][NH2:37].C(O[BH-](OC(=O)C)OC(=O)C)(=[O:42])C.[Na+].[CH3:54][OH:55]>ClCCl.C(O)(=O)C>[F:34][C:35]([F:39])([F:38])[C:54]([OH:42])=[O:55].[C:1]([C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[C:13]3[C:17](=[C:18]([C:20]([NH2:22])=[O:21])[CH:19]=2)[NH:16][CH:15]=[C:14]3[CH:23]2[CH2:28][CH2:27][N:26]([S:29]([CH2:32][CH3:33])(=[O:30])=[O:31])[CH2:25][CH2:24]2)[CH:6]=[C:7]([CH2:9][NH:37][CH2:36][C:35]([F:39])([F:38])[F:34])[CH:8]=1)#[N:2]

참가 물질

7

반응물 4

HCID 887MethanolHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 5049666Sodium triacetoxyborohydrideHCID 866310245-(3-cyano-5-formylphenyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

생성물 1

HCID 866310255-(3-cyano-5-{[(2,2,2-trifluoroethyl)amino]methyl}phenyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide trifluoroacetate수율 6%

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 5-(3-cyano-5-formylphenyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (52 mg, 0.11 mmol) in dichloromethane (3 mL) and methanol (1 mL) was added 20 drops of acetic acid and 2,2,2-trifluoroethanamine (53 μL, 0.66 mmol). The mixture was stirred for 48 h followed by addition of sodium triacetoxyborohydride (140 mg, 0.66 mmol). The mixture was then stirred for 48 h. The resulting reaction was quenched with sodium biocarbonate and brine was added. The organic layer was separated and purified by Gilson Preparatory HPLC to give 3.6 mg of the title compound (6.0%).

후처리

  1. stirringThe mixture was then stirred for 48 h
  2. customThe resulting reaction
  3. customwas quenched with sodium biocarbonate and brine
  4. additionwas added
  5. customThe organic layer was separated
  6. custompurified by Gilson Preparatory HPLC

출처 및 근거

ORD 기록
ord-8a4455858d7b473a8bcb7f4e4606ee69
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354406B2

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