N,N-Dimethylglycine → HCID 66621408, compound

HRID 415184Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([NH2:19])=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)[CH:5]=[CH:6][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.[CH3:30][N:31]([CH3:36])[CH2:32][C:33](O)=[O:34].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C>[CH3:30][N:31]([CH3:36])[CH2:32][C:33]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([NH2:19])=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)[CH:5]=[CH:6][CH:7]=1)=[O:34]

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of 2-(3-aminophenyl)benzo[d]oxazole-4-carboxamide (60 mg, 0.23 mmol) in DMF (3 mL) was added HOBT (35 mg, 0.26 mmol), dimethylglycine (24 mg, 0.23 mmol), DIPEA (91 mg, 0.7 mmol) and EDCI (54 mg, 0.29 mmol). The mixture was stirred at 30° C. for 18 hr. The reaction mixture was purified by pre-HPLC to obtain 2-(3-(2-(dimethylamino)acetamido)phenyl)benzo[d]oxazole-4-carboxamide (30 mg, yield 37%). 1H-NMR (400 MHz, DMSO-d6) δ 2.29 (s, 6H), 3.12 (s, 2H), 7.54-7.58 (m, 2H), 7.95-8.06 (m, 5H), 8.46 (s, 1H), 8.69 (s, 1H), 10.11 (s, 1H); LC-MS (ESI) m/z 339 [M+1]−.

Workup

customThe reaction mixture was purified by pre-HPLC

Sources & evidence

ORD record: ord-c59d59e6e03c491c90bcd250a4655302
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088760B2

Reaction notes

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