Diisopropylethylamine → HCID 67125942, compound

HRID 929968Notes

Reaction equation

HRID 929968 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[F:16][CH2:17][C:18]([C:22]1[O:26][N:25]=[C:24]([NH:27][C:28](=O)[O:29]C2C=CC=CC=2)[CH:23]=1)([CH3:21])[CH2:19][F:20].CCN(C(C)C)C(C)C>C1COCC1.CN(C1C=CN=CC=1)C>[F:20][CH2:19][C:18]([C:22]1[O:26][N:25]=[C:24]([NH:27][C:28](=[O:29])[NH:1][C:2]2[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[CH:6][CH:7]=2)[CH:23]=1)([CH3:21])[CH2:17][F:16]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 688611tert-Butyl (4-aminophenyl)carbamateHCID 66876148Phenyl 5-(1,3-difluoro-2-methylpropan-2-yl)isoxazol-3-ylcarbamate

Product 1

HCID 67125942HCID 67125942, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of tert-butyl 4-aminophenylcarbamate (176 mg, 0.85 mmol) in 5 mL of THF was added phenyl 5-(1,3-difluoro-2-methylpropan-2-yl)isoxazol-3-ylcarbamate (250 mg, 0.85 mmol), DIEA (147 mL, 0.85 mmol), and DMAP (5.2 mg, 0.043 mmol). The resulting mixture was heated at 65° C. for 90 min. LC-MS indicated that the reaction was complete. The organic solvent was removed under reduced pressure and the residue was purified with silica gel column chromatography, eluting with 0-50% EtOAc in hexanes, to give tert-butyl 4-(3-(5-(1,3-difluoro-2-methylpropan-2-yl)isoxazol-3-yl)ureido)phenylcarbamate (350 mg, 95%). LC-MS (ESI) m/z 411 (M+H)+.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. customthe residue was purified with silica gel column chromatography
  3. washeluting with 0-50% EtOAc in hexanes

Sources & evidence

ORD record
ord-79dbce06bbcc42cb905f243b442905e8
Source dataset
uspto-grants-2016_03
Patent number
US09296722B2

Reaction notes

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