Ammonia → HCID 24739540, compound

HRID 1944064Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[S:18][C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[C:11]=1[C:19]([O:21]CC)=O.[NH3:24].C(Cl)Cl>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[S:18][C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[C:11]=1[C:19]([NH2:24])=[O:21]

Participants

Conditions

Temperature: 95 °C

Procedure

A solution of Example 1 (250 mg, 0.56 mmol) in ethanol (5 mL) was added to liquid ammonia (15 mL) and the mixture heated in a Parr apparatus to 95° C. at 800 psi for 18 hours. The volatiles were removed in vacuo to give an oily brown residue. Repeated trituration with ethanol and DCM afforded the title compound as a white solid (18 mg). δH (DMSO-d6) 11.20 (1H, bs), 8.34 (1H, d, J=3.4 Hz), 8.20 (1H, dd, J 8.2, 1.3 Hz), 7.76 (1H, dd, J 10.4, 1.8 Hz), 7.62 (1H, d, J=8.2 Hz), 7.57 (2H, br s), 7.49-7.39 (2H, m). LCMS (ES+) RT 3.11 minutes, 412 (M+H)+.

Workup

customThe volatiles were removed in vacuo
customto give an oily brown residue

Sources & evidence

ORD record: ord-310e2af098414f20905af5ed1fdb096a
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394822B2

Reaction notes

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