Ammonium Chloride → HCID 86683655, compound

HRID 1509284Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:20]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:21][C:22]4[N:27]5[C:28]([C:31]([O:33]CC)=O)=[N:29][N:30]=[C:26]5[CH2:25][O:24][C:23]=4[N:36]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+:44]>[OH-].[NH4+]>[C:31]([C:28]1[N:27]2[C:22]3[CH:21]=[C:20]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:19]([C:16]4[CH:17]=[CH:18][C:13]([C:9]5([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH2:11][CH2:12]5)=[CH:14][CH:15]=4)=[N:36][C:23]=3[O:24][CH2:25][C:26]2=[N:30][N:29]=1)(=[O:33])[NH2:44]

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of ethyl 7-(4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)phenyl)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazine-1-carboxylate (70 mg, 0.123 mmol) and ammonium chloride (10 mg, 0.19 mmol) in ammonium hydroxide (1 ml) was heated to 100° C. for 10 minutes under microwave irradiation. The resulting reaction mixture was concentrated to dryness under reduced pressure and purified by Biotage silica gel chromatography (gradient 0% to 10% ethyl acetate in cyclohexane) to give the title compound (38 mg, 13%). LCMS (Method D): RT=1.347 min, M+1=539. 1H-NMR (500 MHz, CD3OD) δ 9.10 (1H, s), 7.47-7.40 (1H, bs), 7.40-7.37 (2H, d), 7.32-7.27 (6H, m), 5.59 (2H, s), 2.59-2.39 (4H, m), 2.14-2.01 (1H, m), 1.88-1.76 (1H, m), 1.44-1.33 (9H, bs).

Workup

customThe resulting reaction mixture
concentrationwas concentrated to dryness under reduced pressure
custompurified by Biotage silica gel chromatography (gradient 0% to 10% ethyl acetate in cyclohexane)

Sources & evidence

ORD record: ord-de90510074194f53badb6536329c2296
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221838B2

Reaction notes

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