Dimethylamine → HCID 86686099, compound

HRID 1469007Notes

Reaction equation

HRID 1469007 reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:12][CH:13]=2)[N:8]=[C:7]([N:22]2[CH:26]=[C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:24]=[N:23]2)[N:6]=1>C1COCC1>[CH3:1][N:2]([CH3:3])[C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:12][CH:13]=2)[N:8]=[C:7]([N:22]2[CH:26]=[C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:24]=[N:23]2)[N:6]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 86686098HCID 86686098, compound

Product 1

HCID 86686099HCID 86686099, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A THF solution of dimethylamine (2M, 0.44 mL, 0.88 mmol) was added to a solution of the above ethyl 1-(4-chloro-7-phenoxyquinazolin-2-yl)-1H-pyrazole-4-carboxylate (70 mg, 0.18 mmol) and THF (1.4 mL). The mixture was stirred 1 h, and then concentrated. The residue was triturated with ethanol, providing the titled compound (45 mg, 63%). MS (ESI/CI): mass calcd. for C22H21N5O3, 403.1; m/z found, 404.3 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 9.02 (s, 1H), 8.31 (d, J=9.3 Hz, 1H), 8.12 (s, 1H), 7.53 (dd, J=11.1, 4.8 Hz, 2H), 7.32 (t, J=7.4 Hz, 1H), 7.27-7.21 (m, 2H), 7.18 (dd, J=9.3, 2.7 Hz, 1H), 6.96 (d, J=2.7 Hz, 1H), 4.27 (q, J=7.1 Hz, 2H), 3.46 (s, 6H), 1.30 (t, J=7.1 Hz, 3H).

Workup

  1. concentrationconcentrated
  2. customThe residue was triturated with ethanol

Sources & evidence

ORD record
ord-17fb64eb0ebd401caca297c53dca855d
Source dataset
uspto-grants-2015_04
Patent number
US09006251B2

Reaction notes

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