Hydrochloric Acid → HCID 66621311, compound

HRID 415198Notes

Reaction equation

[O:1]=[C:2]([C:6]1[C:11]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[O:14][C:10]=2[CH:9]=[CH:8][CH:7]=1)C(O)=O.C1C=CC2N(O)N=[N:27]C=2C=1.[NH4+].[Cl-].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O>[N:18]1[CH:19]=[CH:20][C:15]([C:13]2[O:14][C:10]3[C:11](=[C:6]([C:2]([NH2:27])=[O:1])[CH:7]=[CH:8][CH:9]=3)[N:12]=2)=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2-oxo-2-(2-(pyridin-4-yl)benzo[d]oxazol-4-yl)acetic acid (120 mg, 0.5 mmol) in DMF (15 mL) was added HOBt (148 mg, 1.1 mmol), NH4Cl (54 mg, 1.0 mmol), DIPEA (387 mg, 3.0 mmol) and EDCI (211 mg, 1.1 mmol). The mixture was stirred at 25° C. for 10 hr., water (10 mL) and 1N aqueous hydrochloric acid was added to the mixture until pH=3, then extracted with ethyl acetate (100 mL×4). The organic phase was washed with saturated sodium bicarbonate solution and brine, concentrated and dried in vacuum. The crude product was purified by preparative HPLC to obtain 2-(pyridin-4-yl)benzo[d]oxazole-4-carboxamide as a solid (17 mg, yield 14%). 1H-NMR (400 MHz, DMSO-d6) δ 7.60-7.64 (t, J=8 Hz, 1H), 8.01-8.03 (d, J=8 Hz, 1H), 8.06-8.08 (d, J=8 Hz, 2H), 8.23-8.24 (d, J=8 Hz, 2H), 8.41 (s, 1H), 8.87 (d, 2H); LC-MS (ESI) m/z 240 [M+1]+.

Workup

extractionextracted with ethyl acetate (100 mL×4)
washThe organic phase was washed with saturated sodium bicarbonate solution and brine
concentrationconcentrated
customdried in vacuum
customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-88cdeac949624c48845ba5532858f986
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088760B2

Reaction notes

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