Diethyl Pyrocarbonate → 1-[(4-fluorophenyl)sulfonyl-methyl-amino]-N-[[3-[4-(trifluoromethoxy)phenyl]phenyl]methyl]cyclopropanecarboxamide

HRID 1479885Notes

Reaction equation

HRID 1479885 reaction equation
[CH3:1][N:2]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:3]1([C:6]([OH:8])=O)[CH2:5][CH2:4]1.CCOC(OC(OCC)=O)=O.[F:30][C:31]([F:48])([F:47])[O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:40]=[C:41]([CH2:45][NH2:46])[CH:42]=[CH:43][CH:44]=2)=[CH:35][CH:34]=1>C1COCC1>[F:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([N:2]([CH3:1])[C:3]2([C:6]([NH:46][CH2:45][C:41]3[CH:42]=[CH:43][CH:44]=[C:39]([C:36]4[CH:37]=[CH:38][C:33]([O:32][C:31]([F:30])([F:47])[F:48])=[CH:34][CH:35]=4)[CH:40]=3)=[O:8])[CH2:4][CH2:5]2)(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 3051Diethyl PyrocarbonateHCID 61032752(4'-(Trifluoromethoxy)-[1,1'-biphenyl]-3-yl)methanamineHCID 903908061-[Methyl-(4-fluorophenyl)sulfonyl-amino]cyclopropanecarboxylic acid

Product 1

HCID 903903091-[(4-fluorophenyl)sulfonyl-methyl-amino]-N-[[3-[4-(trifluoromethoxy)phenyl]phenyl]methyl]cyclopropanecarboxamideYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acid 15A (350 mg, 1.28 mmol) was dissolved in 5 ml of THF and at rt DEPC (0.25 mL, 1.3 mol eq) and [3-[4-(trifluoromethoxy)phenyl]phenyl]methanamine 23B (0.376 g, 1.1 mol eq) were added to the solution. The mixture was stirred at rt overnight then evaporated. he residue was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude by chromatographic column (3:7 EtOAc:Petroleum ether) afforded 100 mg of a white solid. Yield=15% 1HNMR (DMSO, 200 MHz) δ 1.09 (2H, bs), 1.34 (2H, bs), 3.00 (3H, s), 4.35 (2H, d, J=5.8 Hz), 7.43 (8H, m), 7.81 (4H, m), 8.17 (1H, bt); [M+1] 523.9 (C25H22F4N2O4S requires 522.51).

Workup

  1. additionwere added to the solution
  2. customthen evaporated
  3. dissolutionhe residue was dissolved in AcOEt (30 ml)
  4. washwashed with water (1×20 ml) and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe purification of the crude by chromatographic column (3:7 EtOAc:Petroleum ether)

Sources & evidence

ORD record
ord-fc6c2268e4a844958a98cf101247b83c
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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