Carbamic acid, 4-pyridinyl-, phenyl ester → HCID 59175856, compound

HRID 1807769Notes

Reaction equation

[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([OH:33])([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:4][C:3]=1[F:34].[N:35]1[CH:40]=[CH:39][C:38]([NH:41][C:42](=O)[O:43]C2C=CC=CC=2)=[CH:37][CH:36]=1>O1CCOCC1>[F:8][C:7]1[CH:6]=[C:5]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]([OH:33])([C:29]([F:31])([F:32])[F:30])[C:25]([F:26])([F:27])[F:28])=[CH:22][CH:23]=3)[CH2:13][CH2:12]2)=[O:10])[CH:4]=[C:3]([F:34])[C:2]=1[NH:1][C:42]([NH:41][C:38]1[CH:39]=[CH:40][N:35]=[CH:36][CH:37]=1)=[O:43]

Participants

Conditions

Temperature: 80 °C

Procedure

(4-Amino-3,5-difluorophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone (0.342 mmol, 170 mg) and phenyl pyridin-4-ylcarbamate (0.513 mmol, 110 mg) were combined in dioxane (2 mL) and heated to 80° C. overnight in a reactivial. The reaction mixture was concentrated under vacuum and the residue was purified by column chromatography (dichloromethane—4% methanol/dichloromethane) to afford title compound (45 mg). MS (ESI) m/z 618.3 [M+H]+

Workup

concentrationThe reaction mixture was concentrated under vacuum
customthe residue was purified by column chromatography (dichloromethane—4% methanol/dichloromethane)

Sources & evidence

ORD record: ord-0f8618b5504e45dbb958678c5be4457e
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357679B2

Reaction notes

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