Methyl N-(triethylammoniosulfonyl)carbamate → HCID 178434013, compound

HRID 706070Notes

Reaction equation

[C:1]([NH:4][NH:5][C:6](=[O:36])[CH2:7][C:8]1[C:9](=[O:35])[N:10]=[C:11]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([C:31]([F:34])([F:33])[F:32])[CH:25]=3)=[CH:19][CH:18]=2)[NH:12][CH:13]=1)(=O)[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][C:20]2[CH:19]=[CH:18][C:17]([CH2:16][CH2:15][O:14][C:11]3[NH:12][CH:13]=[C:8]([CH2:7][C:6]4[O:36][C:1]([CH3:2])=[N:4][N:5]=4)[C:9](=[O:35])[N:10]=3)=[CH:22][CH:21]=2)=[CH:25][C:26]=1[C:31]([F:34])([F:32])[F:33]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of N′-acetyl-2-(2-{[2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl]oxy}-4-oxo-1,4-dihydro-5-pyrimidinyl)acetohydrazide (26 mg, 0.050 mmol) in THF (5 mL) was added Burgess reagent (17.71 mg, 0.074 mmol). The mixture was heated with a microwave reactor at 130° C. for 0.5 h. Purification via MDAP then afforded the title compound (10 mg, 9.8% yield). LCMS: rt=3.38 min, [M+H+]=507

Workup

customPurification via MDAP

Sources & evidence

ORD record: ord-db502dc82c914b7e97cb0f51807cb03c
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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