Methylamine → HCID 59730775, compound

HRID 130677Notes

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C:15]3[C:24]4[C:19](=[CH:20][C:21]([O:25][CH2:26][CH:27]5[CH2:29][O:28]5)=[CH:22][CH:23]=4)[N:18]=[CH:17][CH:16]=3)=[CH:13][C:8]=2[O:7][C:6]=1[CH3:30])=[O:4].[CH3:31][NH2:32]>C(Cl)Cl.C1COCC1.CO>[OH:28][CH:27]([CH2:29][NH:32][CH3:31])[CH2:26][O:25][C:21]1[CH:20]=[C:19]2[C:24]([C:15]([O:14][C:12]3[CH:11]=[CH:10][C:9]4[C:5]([C:3]([NH:2][CH3:1])=[O:4])=[C:6]([CH3:30])[O:7][C:8]=4[CH:13]=3)=[CH:16][CH:17]=[N:18]2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of 6-[(7-hydroxyquinolin-4-yl)oxy]-N,2-dimethyl-1-benzofuran-3-carboxamide 123-A (1 g, 2.9 mmol), 2-(bromomethyl)oxirane (467 mg, 3.4 mmol) and Cs2CO3 (1.4g, 4.2 mmol( in CH3CN (25 ml) was heated to 65° C. for 3 hours. The solution was extracted with EtOAc. N,2-dimethyl-6-{[7-(oxiran-2-ylmethoxy)quinolin-4-yl]oxy}-1-benzofuran-3-carboxamide 123-B (1.1 g) was isolated by a silica gel column using 1-5% MeOH in CH2Cl2 To a solution of 123-B (150 mg, 0.35 mmol) in THF (5 ml) was added a solution of methylamine in MeOH (1 N, 1 ml). The solution was heated to 65° C. for 2 hours. The crude product was purified by HPLC (10-40% CH3CN/H2O over 30 min.) to give 6-({7-[2-hydroxy-3-(methylamino)propoxy]quinolin-4-yl}oxy)-N,2-dimethyl-1-benzofuran-3-carboxamide 123.

Workup

customThe crude product was purified by HPLC (10-40% CH3CN/H2O over 30 min.)

Sources & evidence

ORD record: ord-0d61a744ae104d44a993304c47e4bf2a
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07381824B2

Reaction notes

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