N,N-Dimethylglycine → HCID 57974326, compound

HRID 1864245Notes

Reaction equation

HRID 1864245 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4]([OH:6])=O.[Cl:8][C:9]1[CH:10]=[C:11]([NH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][C:32]=3[O:34][C@@H:35]([CH3:39])[CH2:36][NH:37][CH3:38])[N:27]=[CH:26][N:25]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1>>[Cl:8][C:9]1[CH:10]=[C:11]([NH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][C:32]=3[O:34][C@@H:35]([CH3:39])[CH2:36][N:37]([CH3:38])[C:4](=[O:6])[CH2:3][N:2]([CH3:7])[CH3:1])[N:27]=[CH:26][N:25]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1

Participants

3

Reactant 2

HCID 673N,N-DimethylglycineHCID 69058100HCID 69058100, compound

Product 1

HCID 57974326HCID 57974326, compoundYield 27%

Procedure

The procedure described in Example 1 was repeated using N,N-dimethylglycine and N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[(1S)-1-methyl-2-(methylamino)ethoxy]quinazolin-4-amine (obtained as described for the R-antipode in Example 2.3, preparation of starting materials) to give the title compound in 27% yield; NMR spectrum (DMSO-d6) 1.37 (d, 3H), 2.06 (s, 6H), 3.08 (s, 3H), 3.23 (dd, 1H), 3.25 (s, 2H), 4.26 (dd, 1H), 5.10 (m, 1H), 5.29 (s, 2H), 7.23 (m, 2H), 7.30 (d, 1H), 7.35 (m, 1H), 7.56 (s, 1H), 7.68 (m, 2H), 7.87 (dt, 1H), 8.13 (d, 1H), 8.44 (s, 1H), 8.58 (d, 1H), 9.90 (s, 1H); Mass Spectrum MH+ 535.

Workup

  1. customobtained
  2. customas described for the R-antipode in Example 2.3, preparation of starting materials)

Sources & evidence

ORD record
ord-1e225f060d7b42d0b420b132f00941b1
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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