Diisopropylethylamine → HCID 71479644, compound

https://huagongshe.com/reaction/1907407

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	5-Chloro-2-picolinic acid	HCID 2762872	—
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	HCID 86762143	HCID 86762143	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 71479644	HCID 71479644	48%

Reaction Steps

A solution of (±)-tert-butyl (4aR,7aR)-7a-(5-amino-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate from step G of Preparation 1 (9 mg), 5-chloropicolinic acid (7 mg), HATU (14 mg), and DIEA (11 μL), in DMF (0.12 mL) was stirred at rt for 2 h, and the crude reaction mixture was subjected to preparative HPLC eluting with 0-100% B (A: 95% H2O/5% MeCN, 10 mM NH4OAc; B: 5% H2O/95% MeCN, 10 mM NH4OAC over 12 min period to give the title compound as a white foam (6 mg, 48%). 1H NMR (500 MHz, CDCl3) δ 9.87 (1H, s), 8.60 (1H, s), 8.26 (1H, d, J=8.5 Hz), 8.02 (1H, br d), 7.92 (1H, dd, J=2.0, 8.0 Hz), 7.72 (1H, m), 7.14 (1H, t, J=10.5 Hz), 4.20 (2H, m), 3.32 (1H, m), 3.02 (1H, m), 2.90 (1H, m), 2.40 (1H, m), 2.24 (1H, m), and 1.51 (9H, s). MS (M+H)+:505.3.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08598161B2
Source dataset	uspto-grants-2013_12
ORD ID	ord-d57a22d129e245d1bdbea5b60070276e
Source note	uspto-grants-2013_12