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

HRID 562071노트

반응식

HRID 562071 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-64f86e7329544f9cb64dea0c875bf69e
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063071B2

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