Tetrahydro-2-furoic acid, (+)- → HCID 11294817, compound

HRID 731901Notes

Reaction equation

HRID 731901 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[C:6]([OH:8])=O.Cl.[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[N:18]=[CH:17][N:16]=[C:15]2[NH:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[C:27]([CH3:38])[CH:26]=1>CN(C)C=O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[N:18]=[CH:17][N:16]=[C:15]2[NH:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH:32]2[CH2:37][CH2:36][N:35]([C:6]([CH:2]3[CH2:3][CH2:4][CH2:5][O:1]3)=[O:8])[CH2:34][CH2:33]2)=[C:27]([CH3:38])[CH:26]=1

Participants

4

Reactant 2

HCID 2734707Tetrahydro-2-furoic acid, (+)-HCID 69053647HCID 69053647, compound

Product 1

HCID 11294817HCID 11294817, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,1′-carbonyldiimidizole (41.38 mg, 0.255 mmol) in N,N-dimethylformamide (1 mL) was added (R)-(+)-tetrahydrofuroic acid (29.6 mg, 0.255 mmol). The reaction was stirred at room temperature for 30 minutes then (6,7-dimethoxy-quinazolin-4-yl)-[3-methyl-4-(piperidin-4-yloxy)-phenyl]-amine hydrochloride was added. The reaction was stirred at room temperature overnight. The following day, the reaction was filtered through a 0.45 μm PTFE membrane filter and purified by preparatory HPLC. 1H NMR (300 MHz, DMSO-d6) δ 9.35 (s, 1H), 8.39 (s, 1H), 8.15 (s, 1H), 7.82 (s, 1H), 7.51(d, d, J=8.71 Hz, 2H), 7.16(s, 1H), 7.05(d, J=8.4 Hz, 1H), (t, J=13.06 Hz, 7.15 Hz, 1H), 3.95(s, 3H), 3.93(s, 3H), 3.75(m, 4H), 3.44(m, 2H), 2.21(s, 3H), 2.03(m, 4H), 1.85(m, 2H), 1.70(m, 2H), LMRS (M+): 493.5, (M−): 491.5.

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. filtrationThe following day, the reaction was filtered through a 0.45 μm PTFE membrane
  3. filtrationfilter
  4. custompurified by preparatory HPLC

Sources & evidence

ORD record
ord-6651f9ca79284abab96833aeebca6307
Source dataset
uspto-grants-2009_09
Patent number
US07585869B2

Reaction notes

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