2-Aminothiazole → N-Ethyl-1,3-thiazol-2-amine

Participants

Role	Name	HCID	Charge
Reactant	2-Aminothiazole	HCID 2155	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Sodium cyanoborohydride	HCID 5003444	—
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	N-Ethyl-1,3-thiazol-2-amine	HCID 13699275	—
Reactant	5-Chloro-3-(4-chloro-3-trifluoromethyl benzenesulfonylamino)-pyridine-2-carboxylic acid	HCID 57942077	—
Product	N-Ethyl-1,3-thiazol-2-amine	HCID 13699275	—
Product	5-Chloro-3(4-chloro-3-(trifluoromethyl)phenysulfonamido)-N-ethyl-(thiazol-2-yl)picolinamide	HCID 66648956	—

Reaction Steps

5-Chloro-3-(4-chloro-3-(trifluoromethyl)phenylsulfonamido)picolinic acid (120 mg, 0.3 mmol), 2-ethylaminothiazole [(50 mg, 0.4 mmol) 2-Ethylaminothiazole was prepared freshly from 2-aminothiazole and acetylaldehyde via standard reductive amination condition using NaCNBH3 as the reducing agent], HATU (190 mg, 0.5 mmol), DIEA (130 mg, 1 mmol) were reacted according to the procedure D to provide the title compound. HPLC purification (20→90% gradient of MeCN-water) provided 5-Chloro-3(4-chloro-3-(trifluoromethyl)phenysulfonamido)-N-ethyl-(thiazol-2-yl)picolinamide: 1H NMR (400 MHz, CDCl3) δ 9.20 (s, 1 H), 8.23 (s, 1 H), 8.07 (s, 1 H), 7.82 (d, 1 H), 7.61 (s, 1 H), 7.46 (d, 1 H), 7.20 (s, 1 H), 6.0 (s, 2H), 4.02 (q, 2H), 1.25 (t, 3H); MS m/z 525.0 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07622583B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-0b2210c5f32c4544a80bf103905ec9c2
Source note	uspto-grants-2009_11