Methylamine → N-methyl-2-(4-{1-[3-({[(2,2,2-trifluoroethyl)amino]carbonyl}amino)phenyl]-1H-benzimidazol-5-yl}phenyl)propanamide

HRID 406983Notes

Reaction equation

HRID 406983 reaction equation
[F:1][C:2]([F:35])([F:34])[CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:9]=[C:10]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([C:23]4[CH:28]=[CH:27][C:26]([CH:29]([CH3:33])[C:30]([OH:32])=O)=[CH:25][CH:24]=4)=[CH:22][C:17]=3[N:16]=[CH:15]2)[CH:11]=[CH:12][CH:13]=1)=[O:6].CN.F[P-](F)(F)(F)(F)F.[N:45]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:49]2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C1COCC1.CN(C)C=O.CO>[CH3:49][NH:45][C:30](=[O:32])[CH:29]([C:26]1[CH:25]=[CH:24][C:23]([C:21]2[CH:20]=[CH:19][C:18]3[N:14]([C:10]4[CH:11]=[CH:12][CH:13]=[C:8]([NH:7][C:5]([NH:4][CH2:3][C:2]([F:35])([F:1])[F:34])=[O:6])[CH:9]=4)[CH:15]=[N:16][C:17]=3[CH:22]=2)=[CH:28][CH:27]=1)[CH3:33]

Participants

8

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 679802542-(4-{1-[3-({[(2,2,2-trifluoroethyl)amino]carbonyl]amino)phenyl]-1H-benzimidazol-5-yl}phenyl)propanoic acid

Product 1

HCID 57386673N-methyl-2-(4-{1-[3-({[(2,2,2-trifluoroethyl)amino]carbonyl}amino)phenyl]-1H-benzimidazol-5-yl}phenyl)propanamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-{1-[3-({[(2,2,2-trifluoroethyl)amino]carbonyl}amino)phenyl]-1H-benzimidazol-5-yl}phenyl)propanoic acid (20.0 mg, 0.0414 mmol) and 2.0 M methylamine in THF (41 μL, 0.083 mmol, Aldrich, Cat. No. 395056) in N,N-dimethylformamide (1 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (23 mg, 0.053 mmol, Adv. ChemTech. Cat. No. RC8105) and N,N-diisopropylethylamine (23 μL, 0.13 mmol). The reaction mixture was stirred at r.t. 2 h., then diluted with MeOH, and purified by RP-HPLC (pH=10) to afford the desired compound. LCMS (M+H)+: m/z=496.2.

Workup

  1. custompurified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-ae132c3554014a7584b197a53d78c69d
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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