Diphenylacetic Acid → N-[5-(2-Chloro-benzyl)-thiazol-2-yl]-2,2-diphenyl-acetamide

HRID 533968Notes

Reaction equation

HRID 533968 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4][C:5]1[S:9][C:8]([NH2:10])=[N:7][CH:6]=1.[C:15]1([CH:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22](O)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4][C:5]1[S:9][C:8]([NH:10][C:22](=[O:23])[CH:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:7][CH:6]=1

Participants

6

Reactant 4

HCID 8333Diphenylacetic AcidHCID 8471TriethylamineHCID 7277455-(2-Chloro-benzyl)-thiazol-2-ylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 1640986N-[5-(2-Chloro-benzyl)-thiazol-2-yl]-2,2-diphenyl-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(2-Chloro-benzyl)-thiazol-2-ylamine (45 mg, 0.20 mmol) and diphenyl-acetic acid (42 mg, 0.20 mmol) were dissolved in N,N-dimethylformamide (1 mL) containing triethylamine (84.1 μL, 0.600 mmol). O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (84 mg, 0.22 mmol) was added and the solution was allowed to stir for 16 hours. The crude product was purified by reverse-phase preparative liquid chromatography (10.3 mg, 0.0246 mmol, 12%). ESI-MS m/z calc. 418.1. found 419.2 (M+1)+ Retention time 3.85 minutes. 1H NMR (400 MHz, DMSO-d6) δ 4.19 (s, 2H), 5.30 (s, 1H), 7.23-7.47 (m, 15H).

Workup

  1. customThe crude product was purified by reverse-phase preparative liquid chromatography (10.3 mg, 0.0246 mmol, 12%)

Sources & evidence

ORD record
ord-f3a11708c53846ff9fba16e6a279ea20
Source dataset
uspto-grants-2014_10
Patent number
US08853415B2

Reaction notes

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