Methanol → HCID 24866351, compound

HRID 506166Notes

Reaction equation

HRID 506166 reaction equation
[C:1]([C:3]1[C:4]([NH:24][C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[NH:30][CH:29]=[CH:28]3)=[C:5]([C:9]2[CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([OH:23])=O)=[CH:17][CH:16]=3)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[N:7][CH:8]=1)#[N:2].F[P-](F)(F)(F)(F)F.[N:41]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:45]2C=CC=CC=2N=N1.CN.CO>CN(C=O)C.CS(C)=O>[C:1]([C:3]1[C:4]([NH:24][C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[NH:30][CH:29]=[CH:28]3)=[C:5]([C:9]2[CH:10]=[C:11]([C:15]3[CH:16]=[CH:17][C:18]([C:21]([NH:41][CH3:45])=[O:23])=[CH:19][CH:20]=3)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[N:7][CH:8]=1)#[N:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 6329MethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 24864531HCID 24864531, compound

Product 1

HCID 24866351HCID 24866351, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3′-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]biphenyl-4-carboxylic acid 134 (40 mg, 0.09 mmol) and BOP (41 mg, 0.09 mmol) in DMF (1 mL) was added methylamine solution in MeOH (2M, 47 uL, 0.09 mmol) followed by TEA (19 uL, 0.14 mmol). The reaction mixture was stirred for 12 h at r.t. The crude reaction mixture was then dissolved in dimethylsulfoxide (DMSO, 1 mL) and purified by reversed phase HPLC to give 16 mg 3′-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-methyl biphenyl-4-carboxamide 196 (39%). MS: 44.2 (M+H); HPLC retention time: 2.10 min.(a).

Workup

  1. customThe crude reaction mixture
  2. custompurified by reversed phase HPLC

Sources & evidence

ORD record
ord-ac581343c81e4550a9b3188eaaaad92d
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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