Methoxyacetic Acid → HCID 57974296, compound

HRID 1864238Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]([OH:6])=O.[NH2:7][CH2:8][C@H:9]([CH3:37])[O:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[C:13]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)=[C:24]([Cl:36])[CH:23]=1)=[N:14][CH:15]=[N:16]2>>[Cl:36][C:24]1[CH:23]=[C:22]([NH:21][C:13]2[C:12]3[C:17](=[CH:18][CH:19]=[CH:20][C:11]=3[O:10][C@@H:9]([CH3:37])[CH2:8][NH:7][C:4](=[O:6])[CH2:3][O:2][CH3:1])[N:16]=[CH:15][N:14]=2)[CH:27]=[CH:26][C:25]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1

Participants

Reactant 2

HCID 12251Methoxyacetic Acid

HCID 69062744HCID 69062744, compound

Product 1

HCID 57974296HCID 57974296, compoundYield 53%

Procedure

The procedure described in Example 1 was repeated using methoxyacetic acid 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 53% yield; NMR spectrum (DMSO-d6) 1.39 (d, 3H), 3.20 (s, 3H), 3.40 (m, 1H), 3.72 (m, 1H), 3.75 (s, 2H), 4.93 (m, 1H), 5.29 (s, 2H), 7.23 (m, 2H), 7.31 (d, 1H), 7.58 (m, 2H), 7.70 (t, 1H), 7.86 (dt, 1H), 7.95 (s, 1H), 8.12 (d, 1H), 8.19 (t, 1H), 8.47 (s, 1H), 8.58 (m, 1H), 9.97 (s, 1H); Mass Spectrum MH+ 508.

Sources & evidence

ORD record: ord-4112f349c0a643d9a3b206a02988cbce
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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