Triethylamine → 1-(4-Methoxy-phenyl)-cyclopropanecarboxylic acid benzothiazol-2-ylamide

HRID 408513

Reaction equation

HRID 408513 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH2:10].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([C:22](O)=[O:23])[CH2:21][CH2:20]2)=[CH:15][CH:14]=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>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:22]([C:19]1([C:16]2[CH:15]=[CH:14][C:13]([O:12][CH3:11])=[CH:18][CH:17]=2)[CH2:21][CH2:20]1)=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8706Benzo(d)thiazol-2-amineHCID 855751-(4-Methoxyphenyl)cyclopropane-1-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 115515661-(4-Methoxy-phenyl)-cyclopropanecarboxylic acid benzothiazol-2-ylamideYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzothiazol-2-ylamine (30. mg, 0.20 mmol) and 1-(4-methoxy-phenyl)-cyclopropanecarboxylic acid (38 mg, 0.20 mmol) were dissolved in N,N-dimethylformamide (DMF, 1 mL) containing triethylamine (84 μL, 0.60 mmol). O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 80 mg, 0.21 mmol) was added and the solution was allowed to stir at room temperature for 16 hours. The crude product was purified by reverse-phase preparative liquid chromatography to yield the pure product (17 mg, 0.052 mmol, 26%). ESI-MS m/z calc. 324.1. found 325.0 (M+1)+. Retention time of 3.48 minutes.

Workup

  1. customThe crude product was purified by reverse-phase preparative liquid chromatography

Sources & evidence

ORD record
ord-c42464d75a4a4067a58a95e9a07da791
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Linked notes

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