2-Phenylbutyric Acid → N-(6-Ethoxy-benzothiazol-2-yl)-2-phenyl-butyramide

HRID 1971508

Reaction equation

HRID 1971508 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]=[C:9]([NH2:11])[S:10][C:6]=2[CH:5]=1)[CH3:2].[C:14]1([CH:20]([CH2:24][CH3:25])[C:21](O)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=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>[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]=[C:9]([NH:11][C:21](=[O:22])[CH:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:24][CH3:25])[S:10][C:6]=2[CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 70122-Phenylbutyric AcidHCID 7192Amino-6-ethoxybenzothiazole, 2-HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 4477449N-(6-Ethoxy-benzothiazol-2-yl)-2-phenyl-butyramide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Ethoxy-benzothiazol-2-ylamine (39 mg, 0.20 mmol) and 2-phenyl-butyric acid (33 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 (17 mg, 0.050 mmol, 25%). ESI-MS m/z calc. 340.1. found 340.9 (M+1)+ Retention time 3.55 minutes.

Workup

  1. customThe crude product was purified by reverse-phase preparative liquid chromatography (17 mg, 0.050 mmol, 25%)

Sources & evidence

ORD record
ord-3266216ef30d4b8393a1472c4b30e26d
Source dataset
uspto-grants-2013_04
Patent number
US08431605B2

Linked notes

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