N,N-Dimethylglycine → HCID 58710729, compound

HRID 1442983Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:27][CH3:28])=[CH:17][C:18]=3[O:20][CH2:21][C@@H:22]3[CH2:26][CH2:25][CH2:24][NH:23]3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:29][N:30]([CH3:35])[CH2:31][C:32](O)=[O:33]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:27][CH3:28])=[CH:17][C:18]=3[O:20][CH2:21][C@@H:22]3[CH2:26][CH2:25][CH2:24][N:23]3[C:32](=[O:33])[CH2:31][N:30]([CH3:35])[CH3:29])[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Reactant 2

HCID 673N,N-Dimethylglycine

HCID 68676425HCID 68676425, compound

Product 1

HCID 58710729HCID 58710729, compoundYield 73%

Procedure

The procedure described in Example 1 was repeated using N-(3-chloro-4-fluoro-phenyl)-7-methoxy-5-[(2S)-pyrrolidin-2-ylmethoxy]-quinazolin-4-amine (96 mg) and N,N-dimethylglycine (27 mg) to give the title compound as a white solid in 73% yield; NMR Spectrum (DMSO-d6) 9.90 (s, 1H), 8.40 (s, 1H), 8.15 (dd, 1H), 7.72-7.62 (m, 1H), 7.40 (t, 1H), 6.88 (d, 1H), 6.78 (d, 1H), 4.66-4.58 (m, 1H), 4.40 (dd, 1H), 4.19 (dd, 1H), 3.90 (s, 3H), 3.66-3.40 (m, 2H), 3.20-3.06 (m, 2H), 2.40 (s, 6H), 2.10-1.82 (m, 4H); MH+ 488.

Sources & evidence

ORD record: ord-d4c0b11b8a4b41649b753b57579621ba
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659279B2

Reaction notes

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