Diisopropylethylamine → HCID 86762145, compound

https://huagongshe.com/reaction/1907406

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	5-Bromopyridine-2-carboxylic acid	HCID 608544	—
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 86762145	HCID 86762145	68.8%

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 (31 mg), 5-bromopicolinic acid (26 mg), HATU (48 mg), and DIEA (44 μL) in DMF (0.41 mL) was stirred at rt for 2 h, and the crude reaction mixture was subjected to preparative HPLC eluting with 0-100% A/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 yellow foam (32 mg, 68%). 1H NMR (500 MHz, CDCl3) δ 9.89 (1H, s), 8.71 (1H, s),8.21 (1H, dd, J=0.4, 8.0 Hz), 8.07 (1H, dd, J=2.0, 8.0 Hz), 8.03 (1H, m), 7.72 (1H, m), 7.14 (1H, t, J=10.5 Hz), 4.15 (2H, m), 3.32 (1H, m), 3.03 (1H, m), 2.90 (1H, m), 2.40 (1H, m), 2.22 (1H, m), and 1.51 (9H, s). MS (M+H)+: 553.3.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08598161B2
Source dataset	uspto-grants-2013_12
ORD ID	ord-cd6d7b1602564600be6a5b61feb44f2d
Source note	uspto-grants-2013_12