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

HRID 1806259Notes

Reaction equation

HRID 1806259 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-8a4455858d7b473a8bcb7f4e4606ee69
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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