N,N-Dimethylglycine → HCID 57974305, compound

HRID 1864269Notes

Reaction equation

[CH3:1][N:2]([CH3:7])[CH2:3][C:4](O)=[O:5].[NH2:8][C@@H:9]([CH3:38])[CH2:10][O:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[C:14]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)=[C:25]([Cl:37])[CH:24]=1)=[N:15][CH:16]=[N:17]2>>[Cl:37][C:25]1[CH:24]=[C:23]([NH:22][C:14]2[C:13]3[C:18](=[CH:19][CH:20]=[CH:21][C:12]=3[O:11][CH2:10][C@@H:9]([NH:8][C:4](=[O:5])[CH2:3][N:2]([CH3:7])[CH3:1])[CH3:38])[N:17]=[CH:16][N:15]=2)[CH:28]=[CH:27][C:26]=1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1

Participants

Reactant 2

HCID 673N,N-Dimethylglycine

HCID 69059443HCID 69059443, compound

Product 1

HCID 57974305HCID 57974305, compoundYield 42%

Procedure

The procedure described in Example 1 was repeated using N,N-dimethylglycine and 5-{[(2S)-2-aminopropyl]oxy}-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine to give the title compound in 42% yield; NMR spectrum (DMSO-d6) 1.21 (d, 3H), 2.05 (s, 6H), 2.60-2.80 (m, 2H), 4.20-4.40 (m, 2H), 4.40-4.60 (m, 1H), 5.30 (s, 2H), 7.15 (m, 1H), 7.22 (m, 1H), 7.35 (m, 2H), 7.54 (m, 2H), 7.70 (t, 1H), 7.90 (t, 1H), 7.98 (m, 2H), 8.48 (s, 1H), 8.59 (d, 1H), 9.76 (s, 1H); Mass spectrum MH+ 521.4.

Sources & evidence

ORD record: ord-7d941ce256894ebc85f5e4e0975d9a34
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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