2-Methanesulfonylacetic acid → HCID 57974316, compound

HRID 1864247Notes

Reaction equation

HRID 1864247 reaction equation
[CH3:1][S:2]([CH2:5][C:6]([OH:8])=O)(=[O:4])=[O:3].[Cl:9][C:10]1[CH:11]=[C:12]([NH:24][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][C:33]=3[O:35][C@@H:36]([CH3:40])[CH2:37][NH:38][CH3:39])[N:28]=[CH:27][N:26]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>>[Cl:9][C:10]1[CH:11]=[C:12]([NH:24][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][C:33]=3[O:35][C@@H:36]([CH3:40])[CH2:37][N:38]([CH3:39])[C:6](=[O:8])[CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[N:28]=[CH:27][N:26]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1

Participants

3

Reactant 2

HCID 37328412-Methanesulfonylacetic acidHCID 69058100HCID 69058100, compound

Product 1

HCID 57974316HCID 57974316, compoundYield 61%

Procedure

The procedure described in Example 1 was repeated using methanesulfonylacetic acid 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 61% yield; NMR spectrum (DMSO-d6) 1.38 (d, 3H), 2.95 (s, 3H), 3.15 (s, 3H), 3.37 (dd, 1H), 4.30 (m, 1H), 4.41 (d, 2H), 5.11 (m, 1H), 5.29 (s, 2H), 7.24 (m, 2H), 7.30 (d, 1H), 7.35 (m, 1H), 7.57 (d, 1H), 7.64 (dd, 1H), 7.70 (t, 1H), 7.86 (dt, 1H), 8.11 (d, 1H), 8.45 (s, 1H), 8.58 (d, 1H), 9.88 (s, 1H); Mass Spectrum MH+ 570.

Workup

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

Sources & evidence

ORD record
ord-4d49ffc586a44b0c8649ef49b8e4a424
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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