Azanium;hydrate → 2-(3-((2-(Dimethylamino)ethylamino)methyl)phenyl)benzo[d]oxazole-7-carboxamide

HRID 415225Notes

Reaction equation

[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][NH:5][CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[O:14][C:15]3[C:21]([C:22](OC)=[O:23])=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:10]=[CH:11][CH:12]=1.O.[NH4+:28]>C(O)C>[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][NH:5][CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[O:14][C:15]3[C:21]([C:22]([NH2:28])=[O:23])=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 30 °C

Procedure

Methyl 2-(3-((2-(dimethylamino)ethylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylate (100 mg, 0.28 mmol) and ammonium water (58.8 mg, 1.68 mmol) were added to ethanol (30 mL) and the mixture was stirred at 30° C. for 1 hr. Evaporation under reduced pressure and purification with pre-HPLC gave 2-(3-((2-(dimethylamino)ethylamino)methyl)phenyl)benzo[d]oxazole-7-carboxamide (10.0 mg, yield 11%). 1H-NMR (400 MHz, DMSO-d6) δ 2.85 (s, 6H), 3.37-3.42 (d, J=20 Hz, 4H), 4.36 (s, 2H), 7.48-7.52 (t, J=8 Hz, 1H), 7.71-7.97 (m, 6H), 8.35-8.37 (d, J=8 Hz, 1H), 8.43 (s, 1H); LC-MS (ESI) m/z 339 [M+1]+.

Workup

customEvaporation
customunder reduced pressure and purification

Sources & evidence

ORD record: ord-0ec77df83c914b6887e2bd3b9208b588
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088760B2

Reaction notes

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