Diphenylacetic Acid → HCID 86600157, compound

HRID 1971501Notes

Reaction equation

HRID 1971501 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][C:5]1[N:6]=[C:7]([NH2:10])[S:8][CH:9]=1.[C:12]1([CH:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19](O)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=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>[CH3:1][O:2][C:3](=[O:11])[CH2:4][C:5]1[N:6]=[C:7]([NH:10][C:19](=[O:20])[CH:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[S:8][CH:9]=1

Participants

6

Reactant 4

HCID 8333Diphenylacetic AcidHCID 8471TriethylamineHCID 738059Methyl (2-amino-1,3-thiazol-4-yl)acetateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86600157HCID 86600157, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2-Amino-thiazol-4-yl)-acetic acid methyl ester (45 mg, 0.20 mmol) and diphenyl-acetic acid (37 mg, 0.20 mmol) were dissolved in N,N-dimethylformamide (2 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 (29.4 mg, 0.0802 mmol, 40. %). ESI-MS m/z calc. 380.1. found 381.3 (M+1)+ Retention time 3.28 minutes.

Workup

  1. customThe crude product was purified by reverse-phase preparative liquid chromatography (29.4 mg, 0.0802 mmol, 40. %)

Sources & evidence

ORD record
ord-275d0173285e42ecae793754214977dc
Source dataset
uspto-grants-2013_04
Patent number
US08431605B2

Reaction notes

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