N,N-Dimethylglycine → HCID 57974310, compound

HRID 1864237Notes

Reaction equation

HRID 1864237 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4](O)=[O:5].[NH2:8][CH2:9][C@H:10]([CH3:38])[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][C@@H:10]([CH3:38])[CH2:9][NH:8][C:4](=[O:5])[CH2:3][N:2]([CH3:7])[CH3:1])[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

3

Reactant 2

HCID 673N,N-DimethylglycineHCID 69062744HCID 69062744, compound

Product 1

HCID 57974310HCID 57974310, compoundYield 49%

Procedure

The procedure described in Example 1 was repeated using N,N-dimethylglycine and 5-[(1S)-2-amino-1-methylethoxy]-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine (obtained as described in Example 36, preparation of starting materials) to give the title compound in 49% yield; NMR spectrum (DMSO-d6) 1.38 (d, 3H), 2.07 (s, 6H), 2.80 (s, 2H), 3.41 (m, 1H), 3.73 (m, 1H), 4.93 (m, 1H), 5.29 (s, 2H), 7.23 (m, 2H), 7.30 (d, 1H), 7.35 (t, 1H), 7.59 (m, 2H), 7.70 (t, 1H), 7.86 (td, 1H), 8.12 (m, 2H), 8.47 (s, 1H), 8.58 (d, 1H), 9.96 (s, 1H); Mass Spectrum MH+ 521.

Sources & evidence

ORD record
ord-68b3243ac7464ea6962de5cf8d554454
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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