Water → tert-butyl (cyclopropylmethyl)[trans-2-(4-{[(1-methyl-1H-pyrazol-4-yl)carbonyl]amino}phenyl)cyclopropyl]carbamate

HRID 922555Notes

Reaction equation

HRID 922555 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[N:11]([CH2:19][CH:20]2[CH2:22][CH2:21]2)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.[CH3:23][N:24]1[CH:28]=[C:27]([C:29](O)=[O:30])[CH:26]=[N:25]1.Cl.C(N=C=NCCCN(C)C)C.O>CN(C=O)C>[C:14]([O:13][C:12](=[O:18])[N:11]([CH2:19][CH:20]1[CH2:22][CH2:21]1)[C@@H:9]1[CH2:10][C@H:8]1[C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:29]([C:27]2[CH:26]=[N:25][N:24]([CH3:23])[CH:28]=2)=[O:30])=[CH:3][CH:4]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6431601-Methyl-1H-pyrazole-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86729891Tert-butyl [trans-2-(4-aminophenyl)cyclopropyl](cyclopropylmethyl)carbamate

Product 1

HCID 86729931tert-butyl (cyclopropylmethyl)[trans-2-(4-{[(1-methyl-1H-pyrazol-4-yl)carbonyl]amino}phenyl)cyclopropyl]carbamateYield 98.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl [trans-2-(4-aminophenyl)cyclopropyl](cyclopropylmethyl)carbamate (85.8 mg) and 1-methyl-1H-pyrazole-4-carboxylic acid (42.9 mg) in DMF (1.42 mL) was added N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (82 mg). The mixture was stirred at room temperature overnight, and poured into water. The mixture was extracted with ethyl acetate, and the extract was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (114.8 mg).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extract was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5838d075c09f4388b7c5bad44ffc82aa
Source dataset
uspto-grants-2016_03
Patent number
US09278931B2

Reaction notes

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