Triethylamine → 2,2,3,3-Tetramethylcyclopropanecarboxylic acid [3-(2-methoxy-ethy)-5-methyl-4-phenyl-3H-thiazol-2-ylidene]-amide

HRID 78421

Reaction equation

HRID 78421 reaction equation
Br.[CH3:2][O:3][CH2:4][CH2:5][N:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:9]([CH3:17])[S:8][C:7]1=[NH:18].[CH3:19][C:20]1([CH3:28])[C:22]([CH3:24])([CH3:23])[CH:21]1[C:25](O)=[O:26].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[CH3:2][O:3][CH2:4][CH2:5][N:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:9]([CH3:17])[S:8][C:7]1=[N:18][C:25]([CH:21]1[C:22]([CH3:24])([CH3:23])[C:20]1([CH3:28])[CH3:19])=[O:26]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1521152,2,3,3-Tetramethylcyclopropanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 686222923-(2-methoxyethyl)-5-methyl-4-phenyl-3H-thiazol-2-ylideneamine hydrobromide

Product 1

HCID 686218512,2,3,3-Tetramethylcyclopropanecarboxylic acid [3-(2-methoxy-ethy)-5-methyl-4-phenyl-3H-thiazol-2-ylidene]-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product of Example 119A (290 mg, 1.16 mmol), 2,2,3,3-tetramethylcyclopropanecarboxylic acid (182 mg, 1.28 mmol), HATU (661 mg, 1.74 mmol) and triethylamine (0.97 mL, 6.96 mmol) in 15 mL of DMF was processed according to the method of Example 2B to provide the title compound: 1H NMR (400 MHz, DMSO-d6) δ 1.17 (s, 6H) 1.26 (s, 6H) 1.49 (s, 1H) 2.01 (s, 3H) 3.02 (s, 3H) 3.43 (t, J=6.0 Hz, 2H) 4.06 (t, J=5.8 Hz, 2H) 7.39-7.43 (m, 2H) 7.50-7.57 (m, 3H); MS (DCI/NH3) m/z 373 (M+H)+.

Sources & evidence

ORD record
ord-2d0b18ead29c4ac9909183c9b49cdd7d
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

Loading…