Methoxyacetic Acid → N-[(2R)-2-({4-[3-chloro-4-hydroxyanilino]quinazolin-5-yl}oxy)propyl]-2-methoxyacetamide

HRID 1864194Notes

Reaction equation

HRID 1864194 reaction equation
[NH2:1][CH2:2][C@@H:3]([CH3:24])[O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([Cl:23])[CH:17]=1)=[N:8][CH:9]=[N:10]2.[CH3:25][O:26][CH2:27][C:28](O)=[O:29]>>[Cl:23][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[OH:22])[NH:15][C:7]1[C:6]2[C:11](=[CH:12][CH:13]=[CH:14][C:5]=2[O:4][C@H:3]([CH3:24])[CH2:2][NH:1][C:28](=[O:29])[CH2:27][O:26][CH3:25])[N:10]=[CH:9][N:8]=1

Participants

3

Reactant 2

HCID 12251Methoxyacetic AcidHCID 575019434-({5-[(1R)-2-amino-1-methylethoxy]quinazolin-4-yl}amino)-2-chlorophenol

Product 1

HCID 69058964N-[(2R)-2-({4-[3-chloro-4-hydroxyanilino]quinazolin-5-yl}oxy)propyl]-2-methoxyacetamideYield 83%

Procedure

4-({5-[(1R)-2-Amino-1-methylethoxy]quinazolin-4-yl}amino)-2-chlorophenol was reacted with methoxyacetic acid using an analogous process to that described in Example 3 (preparation of starting materials) to give N-[(2R)-2-({4-[3-chloro-4-hydroxyanilino]quinazolin-5-yl}oxy)propyl]-2-methoxyacetamide in 83% yield; NMR spectrum (DMSO-d6) 1.4 (d, 3H), 3.1 (s, 3H), 3.35-3.45 (m, 1H), 3.72-3.85 (m, 3H), 4.95-5.05 (m, 1H), 7.05 (d, 1H), 7.31 (d, 1H), 7.4 (dd, 1H), 7.48 (d, 1H), 7.81 (m, 1H), 7.95 (t, 1H), 8.25 (t, 1H), 8.8 (s, 1H), 10.39 (s, 1H), 10.74 (s, 1H) Mass spectrum MH+ 417.

Workup

  1. customdescribed in Example 3 (preparation of starting materials)

Sources & evidence

ORD record
ord-acb1a89f3dbf41a78cc0a3869a82b64e
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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