N,N-Dimethylglycine → HCID 58710711, compound

HRID 1443005Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:24][CH3:25])=[CH:13][C:14]=2[O:16][CH2:17][C@@H:18]2[NH:22][CH2:21][C@@H:20]([OH:23])[CH2:19]2)[N:9]=[CH:8][N:7]=1.[CH3:30][N:31]([CH3:36])[CH2:32][C:33](O)=[O:34]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:24][CH3:25])=[CH:13][C:14]=2[O:16][CH2:17][C@@H:18]2[N:22]([C:33](=[O:34])[CH2:32][N:31]([CH3:36])[CH3:30])[CH2:21][C@@H:20]([OH:23])[CH2:19]2)[N:9]=[CH:8][N:7]=1

Participants

Reactant 2

HCID 673N,N-Dimethylglycine

HCID 68676927HCID 68676927, compound

Product 1

HCID 58710711HCID 58710711, compoundYield 73%

Procedure

The procedure described in Example 20 was repeated using (3S,5R)-5-[({4-[3-chloro-4-fluoroanilino]-7-methoxyquinazolin-5-yl}oxy)methyl]pyrrolidin-3-ol (185 mg) with N,N-dimethylglycine (50 mg) to give the title compound as a white solid in 73% yield; NMR spectrum (DMSO-d6) 9.93 (s, 1H), 8.45 (s, 1H), 8.15 (dd, 1H), 7.76-7.70 (m, 1H), 7.45 (t, 1H), 6.83 (s, 2H), 5.09-5.08 (m, 1H), 4.70-4.66 (m, 1H), 4.45-4.40 (m, 2H), 4.28-4.23 (m, 1H), 3.93 (s, 3H), 3.62-3.49 (m, 2H), 3.20 (d, 1H), 3.00 (d, 1H), 2.21 (s, 6H), 2.06-2.02 (m, 2H); Mass spectrum MH+ 504.

Sources & evidence

ORD record: ord-7f45b990537d40c2b9acedbf304dc42b
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659279B2

Reaction notes

Loading…