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

HRID 1037848Notes

Reaction equation

HRID 1037848 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-7f3adda3579c4068acf3b9120d557a54
Source dataset
uspto-grants-2013_10
Patent number
US08546583B2

Reaction notes

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