1,1-dimethylethyl 3-[({3-[(1-methylethyl)oxy]-5-[(4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]phenyl}carbonyl)amino]-1H-pyrazole-1-carboxylate → HCID 178458722, compound

HRID 548761Notes

Reaction equation

HRID 548761 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([C:25]([NH:27][C:28]2[CH:32]=[CH:31][N:30](C(OC(C)(C)C)=O)[N:29]=2)=[O:26])[CH:8]=[C:9]([O:11][C:12]2[CH:24]=[CH:23][C:15]3[C:16](=[O:22])[N:17]([CH3:21])[CH2:18][CH2:19][O:20][C:14]=3[CH:13]=2)[CH:10]=1)[CH3:3]>CO>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[C:7]([CH:8]=[C:9]([O:11][C:12]2[CH:24]=[CH:23][C:15]3[C:16](=[O:22])[N:17]([CH3:21])[CH2:18][CH2:19][O:20][C:14]=3[CH:13]=2)[CH:10]=1)[C:25]([NH:27][C:28]1[CH:32]=[CH:31][NH:30][N:29]=1)=[O:26])[CH3:1]

Participants

3

Reactant 1

HCID 576631971,1-dimethylethyl 3-[({3-[(1-methylethyl)oxy]-5-[(4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]phenyl}carbonyl)amino]-1H-pyrazole-1-carboxylate

Product 1

HCID 178458722HCID 178458722, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,1-dimethylethyl 3-[({3-[(1-methylethyl)oxy]-5-[(4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]phenyl}carbonyl)amino]-1H-pyrazole-1-carboxylate (42 mg, 0.08 mmol), in methanol (2 mL) was heated at 140° C. in a microwave reactor for 30 minutes. The solution was cooled to RT and pressure, the methanol evaporated in vacuo to a residue which was chromatographed on silica, eluting with ethyl acetate, to give the desired compound (13 mg). 1H NMR δ (CDCl3): 1.3 (d, 6H), 3.15 (s, 3H), 3.5 (t, 2H), 4.3 (t, 2H), 4.5 (m, 1H), 6.5 (s, 1H), 6.7 (m, 2H), 6.75 (s, 1H), 7.1 (d, 1H), 7.25 (d, 1H), 7.45 (d, 1H), 7.8 (d, 1H), 9.4 (s, 1H); m/z 437 (M+H)+

Workup

  1. custompressure, the methanol evaporated in vacuo to a residue which
  2. customwas chromatographed on silica
  3. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-79eb027bd08d4d8c878833b11d1eab02
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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