Neopentylamine → (2,2-Dimethylpropyl)-5-[6-(4-fluorophenyl)-imidazo[2,1-b]oxazol-5-yl]-2-nitrophenylamine

HRID 1711775Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 5-(3-fluoro-4-nitrophenyl)-6-(4-fluorophenyl)-imidazo[2,1-b]oxazole (0.80 g, 2.2 mmol; Preparation #C.1) in ACN (6.0 mL) was added TEA (0.63 mL, 4.5 mmol) and 2,2-dimethylpropylamine (0.24 g, 2.7 mmol; TCI). The reaction was heated at about 80° C. for about 4 h then cooled to about 4° C. The resulting solid was filtered, washing with cold ACN (ca. 4° C.), and dried in a vacuum oven at about 55-65° C. to give the title compound (0.89 g, 96%): LC/MS (Table 1, Method b) Rt=2.62 min; MS m/z: 409.2 (M+H)+.

Workup

temperaturethen cooled to about 4° C
filtrationThe resulting solid was filtered
washwashing with cold ACN (ca. 4° C.)
customdried in a vacuum oven at about 55-65° C.

Sources & evidence

ORD record: ord-cb0286a577154a08968d7d0f6c3efb3e
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790741B2

Reaction notes

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