Diisopropylethylamine → HCID 86762150, compound

HRID 1907412Notes

Reaction equation

HRID 1907412 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.[C:26]([C:28]1[CH:29]=[CH:30][C:31]([C:34](O)=[O:35])=[N:32][CH:33]=1)#[N:27].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>[C:26]([C:28]1[CH:29]=[CH:30][C:31]([C:34]([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:35])=[N:32][CH:33]=1)#[N:27]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 124007345-Cyanopyridine-2-carboxylic acidHCID 86762143HCID 86762143, compound

Product 1

HCID 86762150HCID 86762150, compoundYield 41%

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 from step G of Preparation 1 (9 mg), 5-cyanopicolinic acid (6 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 (5 mg, 41%). 1H NMR (500 MHz, CDCl3) δ 9.90 (1H, s), 8.94 (1H, s), 8.45 (1H, d, J=8.0 Hz), 8.24 (1H, dd, J=2.0, 8.5 Hz), 8.03 (1H, m), 7.72 (1H, m), 4.10-4.25 (2H, m), 3.32 (1H, m), 3.02 (1H, m), 2.90 (1H, m), 2.42 (1H, m), and 2.23 (1H, m) and 1.51 (9H, s). MS (M+H)+: 498.2.

Workup

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

Sources & evidence

ORD record
ord-3852942491264f5b8782e3df1bbd82fb
Source dataset
uspto-grants-2013_12
Patent number
US08598161B2

Reaction notes

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