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

HRID 562071ノート

反応式

HRID 562071 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-64f86e7329544f9cb64dea0c875bf69e
出典データセット
uspto-grants-2011_11
特許番号
US08063071B2

反応ノート

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