Diisopropylethylamine → HCID 59200049, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Sodium Bicarbonate	HCID 516892	—
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	2-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acid	HCID 61702587	—
Reactant	HCID 68552172	HCID 68552172	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 59200049	HCID 59200049	36%

Reaction Steps

A mixture of 3-methyl-pyrrolo[3,2-c]pyridin-1-ylamine (224 mg, 1.52 mmol), 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (354 mg, 1.52 mmol), HATU (693 mg, 1.82 mmol) and DIPEA (593 mg, 4.59 mmol) in DMF (8 mL) is heated at 1500 C. for 1 h. The reaction is quenched with water, NaHCO3 (168 mg, 2 mmol) is added and the mixture is extracted with EtOAc. The organic layer is separated, dried (Na2SO4), filtered and concentrated. The residue is first purified by silica gel column chromatography eluting with 10% MeOH in DCM and then recrystallized from EtOAc to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[3,2-c]pyridin-1-yl)-amide (198 mg). MS: 362 (M+H); 1H NMR (300 MHz, CD3OD): δ 9.12 (s, 1H), 8.86 (s, 1H), 8.35 (d, 1H), 8.15-8.31 (m, 2H), 7.47-7.60 (m, 2H), 7.35 (s, 1H), 7.29 (t, 1H), 2.84 (s, 3H), 2.44 (s, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08258130B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-63f22b8dbdc04c0786c484fa6467207c
Source note	uspto-grants-2012_09