Methyl N-(triethylammoniosulfonyl)carbamate → tert-butyl {3-[(4-{difluoro[5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}benzoyl)amino]-1-phenyl-1H-pyrazol-4-yl}carbamate

HRID 913253Notes

Reaction equation

[F:1][C:2]([C:18]1[CH:45]=[CH:44][C:21]([C:22]([NH:24][C:25]2[C:29]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:28][N:27]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:26]=2)=[O:23])=[CH:20][CH:19]=1)([F:17])[C:3]([NH:5][NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])=O.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[F:1][C:2]([F:17])([C:3]1[O:16][C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])=[N:6][N:5]=1)[C:18]1[CH:45]=[CH:44][C:21]([C:22]([NH:24][C:25]2[C:29]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:34])[CH3:35])=[CH:28][N:27]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:26]=2)=[O:23])=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of tert-butyl {3-[(4-{1,1-difluoro-2-[2-(2-methoxybenzoyl)hydrazino]-2-oxoethyl}benzoyl)amino]-1-phenyl-1H-pyrazol-4-yl}carbamate (0.05 g, 0.08 mmol) in THF (2 mL) was added Burgess reagent (38 mg, 0.16 mmol) and the reaction was sealed and heated to 100° C. for 10 minutes under microwave irradiation. The reaction was evaporated to dryness and purified by reverse phase chromatography (5/95 acetonitrile/water to 95/5 acetonitrile/water) to give tert-butyl {3-[(4-{difluoro[5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}benzoyl)amino]-1-phenyl-1H-pyrazol-4-yl}carbamate as a white solid. ESIMS calcd 603.2 (M++H), found 603.2 (M++H).

Workup

customthe reaction was sealed
customThe reaction was evaporated to dryness
custompurified by reverse phase chromatography (5/95 acetonitrile/water to 95/5 acetonitrile/water)

Sources & evidence

ORD record: ord-d412888e5b0b4b9e8bbffd68d55420f3
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026260B2

Reaction notes

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