Triethylamine → 2,2,3,3-Tetramethylcyclopropanecarboxylic acid [3-(2-methoxy-ethy)-4,5,6,7-tetrahydro-3H-benzothiazol-2-ylidene]-amide

HRID 78424

Reaction equation

HRID 78424 reaction equation
Br.[CH3:2][O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[S:8][C:7]1=[NH:15].[CH3:16][C:17]1([CH3:25])[C:19]([CH3:21])([CH3:20])[CH:18]1[C:22](O)=[O:23].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]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[S:8][C:7]1=[N:15][C:22]([CH:18]1[C:19]([CH3:21])([CH3:20])[C:17]1([CH3:25])[CH3:16])=[O:23]

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 668590283-(2-methoxy-ethyl)-4,5,6,7-tetrahydro-3H-benzothiazol-2-ylideneamine hydrobromide

Product 1

HCID 686237472,2,3,3-Tetramethylcyclopropanecarboxylic acid [3-(2-methoxy-ethy)-4,5,6,7-tetrahydro-3H-benzothiazol-2-ylidene]-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product of Example 121A (156 mg, 0.55 mmol), 2,2,3,3-tetramethylcyclopropanecarboxylic acid (94 mg, 0.66 mmol), HATU (479 mg, 0.83 mmol) and triethylamine (0.46 mL, 3.30 mmol) in 10 mL of DMF was processed according to the method of Example 2B to provide the title compound: 1H NMR (500 MHz, DMSO-d6) δ 1.16 (s, 6H) 1.23 (s, 6H) 1.45 (s, 1H) 1.69-1.82 (m, 4H) 2.43-2.48 (m, 2H) 2.54-2.59 (m, 2H) 3.24 (s, 3H) 3.60 (t, J=5.3 Hz, 2H) 4.16 (t, J=5.3 Hz, 2H); MS (DCI/NH3) m/z 337 (M+H)+.

Sources & evidence

ORD record
ord-3d6c691c15194c04a64248e17a6ade20
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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