5-Tert-butyl-3-isocyanato-1,2-oxazole → HCID 24889893, compound

HRID 1161724Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([CH:15]=2)[C:13]2[CH:16]=[CH:17][C:18]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:19][C:12]=2[S:11]3)=[CH:4][CH:3]=1.[C:27]([C:31]1[O:35][N:34]=[C:33]([N:36]=[C:37]=[O:38])[CH:32]=1)([CH3:30])([CH3:29])[CH3:28]>C1(C)C=CC=CC=1>[C:27]([C:31]1[O:35][N:34]=[C:33]([NH:36][C:37]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:9]=[C:10]4[N:14]([CH:15]=3)[C:13]3[CH:16]=[CH:17][C:18]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:19][C:12]=3[S:11]4)=[CH:6][CH:7]=2)=[O:38])[CH:32]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of ethyl 3-[2-(4-aminophenyl)imidazo[2,1-b][1,3]benzothiazol-7-yl]propanoate (3.80 g, 10.4 mmol) from Step C and 5-tert-butyl-3-isocyanatoisoxazole (2.08 g, 12.5 mmol) in toluene (80 mL) was heated at 110° C. over night. A precipitate was formed, collected by filtration, washed with ether, and dried under high vacuum to give the title compound as a white solid (5.056 g, 91%). 1H NMR (DMSO-d6) δ 9.62 (s, 1H), 9.08 (s, 1H), 8.70 (s, 1H), 7.91 (s, 1H), 7.89 (d, 1H), 7.79 (d, 2H), 7.54 (d, 2H), 7.46 (d, 1H), 6.53 (s, 1H), 4.06 (q, 2H), 2.98 (t, 2H), 2.70 (t, 2H), 1.30 (s, 9H), 1.15 (t, 3H); LC-MS: ESI 532 (M+H)+.

Workup

customA precipitate was formed
filtrationcollected by filtration
washwashed with ether
customdried under high vacuum

Sources & evidence

ORD record: ord-6858f9e12c984d41b44d0f16f9fe43a5
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820657B2

Reaction notes

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