Diisopropylethylamine → HCID 86762145, compound

HRID 1907406Notes

Reaction equation

HRID 1907406 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:25])=[C:6]([C@:8]23[O:16][CH2:15][CH2:14][C@H:13]2[CH2:12][S:11][C:10]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[N:9]3)[CH:7]=1.[Br:26][C:27]1[CH:28]=[CH:29][C:30]([C:33](O)=[O:34])=[N:31][CH:32]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([F:25])=[C:6]([C@:8]34[O:16][CH2:15][CH2:14][C@H:13]3[CH2:12][S:11][C:10]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[N:9]4)[CH:7]=2)=[O:34])=[N:31][CH:32]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6085445-Bromopyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86762143HCID 86762143, compound

Product 1

HCID 86762145HCID 86762145, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  1. customthe crude reaction mixture
  2. washeluting with 0-100% A/B (A: 95% H2O/5% MeCN, 10 mM NH4OAc

Sources & evidence

ORD record
ord-cd6d7b1602564600be6a5b61feb44f2d
Source dataset
uspto-grants-2013_12
Patent number
US08598161B2

Reaction notes

Loading…