4-Amino-1-butanol → 4-{4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-ylamino}-butan-1-ol

HRID 1876178Notes

Reaction equation

HRID 1876178 reaction equation
Cl.Cl[C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[NH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28]>>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([N:13]([CH3:14])[C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=[C:3]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[N:12]=2)=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 258684-Amino-1-butanolHCID 86639964(2-Chloroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine hydrochloride

Product 1

HCID 592421214-{4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-ylamino}-butan-1-ol

Procedure

The title compound was prepared from (2-chloro-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine hydrochloride (81 mg, 0.24 mmol) and 4-amino-butan-1-ol (69 μL, 0.75 mmol) by a procedure similar to Example 180, yielding a pale yellow oil (55 mg; 65%). 1H NMR (CDCl3) δ 7.48 (m, 1H), 7.38 (m, 1H), 7.12 (m, 2H), 6.91 (m, 2H), 6.81 (m, 1H),6.69 (m, 1H), 3.84 (s, 3H), 3.78 (t, J=6 Hz, 2H), 3.60 (m, 2H), 3.53 (s, 3H), 1.82 (m, 2H), 1.73 (m, 2H); LC-MS (ESI+; 353 ([M+H]+)).

Workup

  1. customyielding a pale yellow oil (55 mg; 65%)

Sources & evidence

ORD record
ord-612ff2aac49a41c997ed6653ea830572
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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