Ammonia → HCID 68456408, compound

HRID 30429Notes

Reaction equation

[NH:1]([C:8]1[C:16]2[CH:15]=[CH:14][C:13](=[O:17])[N:12]([C:18]3[CH:22]=[CH:21][S:20][CH:19]=3)[C:11]=2[S:10][C:9]=1[C:23]([O:25]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCCO)C.[NH3:34]>>[NH:1]([C:8]1[C:16]2[CH:15]=[CH:14][C:13](=[O:17])[N:12]([C:18]3[CH:22]=[CH:21][S:20][CH:19]=3)[C:11]=2[S:10][C:9]=1[C:23]([NH2:34])=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 8076Glycol monoethyl ether

HCID 68457218HCID 68457218, compound

Product 1

HCID 68456408HCID 68456408, compound

Conditions

Temperature: 80 °C

Procedure

A mixture of Example 64 (129 mg), 2-ethoxyethanol and liquid ammonia was placed in a sealed pressure vessel and heated at 80° C. and 400 p.s.i. for 24 h. The volatiles were removed in vacuo and the residue purified by column chromatography (silica, 50% to 100% EtOAc in hexane) to give the title compound (20 mg). δH (CDCl3) 8.75 (1H, br s), 7.36-7.34 (2H, m), 7.16-7.11 (2H, m), 7.03 (1H, d, J 9.7 Hz), 6.99-6.88 (4H, m), 6.17 (1H, d, J 9.7 Hz), 5.47 (2H, br s). LCMS (ES+) RT 2.927 minutes, 368 (M+H)+

Workup

customThe volatiles were removed in vacuo
customthe residue purified by column chromatography (silica, 50% to 100% EtOAc in hexane)

Sources & evidence

ORD record: ord-6f8f55cface340e9901090f51f5175a9
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423047B2

Reaction notes

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