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

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	2,2,3,3-Tetramethylcyclopropanecarboxylic acid	HCID 152115	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	3-(2-methoxy-ethyl)-4,5,6,7-tetrahydro-3H-benzothiazol-2-ylideneamine hydrobromide	HCID 66859028	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2,2,3,3-Tetramethylcyclopropanecarboxylic acid [3-(2-methoxy-ethy)-4,5,6,7-tetrahydro-3H-benzothiazol-2-ylidene]-amide	HCID 68623747	—

Reaction Steps

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)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08841334B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-3d6c691c15194c04a64248e17a6ade20
Source note	uspto-grants-2014_09