Diisopropylethylamine → HCID 59199972, compound

https://huagongshe.com/reaction/2382097

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
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 68553177	HCID 68553177	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 59199972	HCID 59199972	9.9%

Reaction Steps

A mixture of 3-methyl-pyrrolo[2,3-c]pyridin-1-ylamine (224 mg, 1.53 mmol), 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (354 mg, 1.53 mmol), HATU (693 mg, 1.82 mmol) and DIPEA (593 mg, 4.59 mmol) in DMF (8 mL) is stirred at 1500 C. for 1 h. The reaction is quenched with water, extracted with EtOAc. The organic layer is dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0-100% EtOAc in heptane to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[2,3-c]pyridin-1-yl)-amide (55 mg). MS: 362 (M+H); 1H NMR (300 MHz, CD3OD): δ 9.15 (s, 1H), 8.69 (s, 1H), 8.37 (d, 1H), 8.24 (s, 1H), 8.20 (d, 1H), 7.68 (d, 1H), 7.55 (q, 1H), 7.47 (s, 1H), 7.29 (t, 1H), 2.84(s, 3H), 2.39 (s, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08258130B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-1d1d9bff0a434c68bf371a8a9cb3414d
Source note	uspto-grants-2012_09