Ammonia → HCID 57527000, compound

HRID 1452588Notes

Reaction equation

HRID 1452588 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH:22]=[C:21]([C:23]([OH:25])=O)[CH:20]=[N:19]2)=[C:14]([F:26])[CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.[N:34]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(CC)CC)C.N>ClCCl.C(O)C>[NH2:34][C:23]([C:21]1[CH:20]=[N:19][N:18]([C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:13][C:14]=2[F:26])[CH:22]=1)=[O:25]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 2724699PyBOPHCID 57526969HCID 57526969, compound2×

Product 1

HCID 57527000HCID 57527000, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-(4-{[Benzyloxycarbonyl]amino}-2-fluorophenyl)-1H-pyrazole-4-carboxylic acid (1.1 g, 3.1 mmol) (Intermediate 41) and benzotriazole-1-yl-oxy-trispyrrolidinophosphonium hexafluorophosphate (PyBob) (1.61 g, 3.1 mmol) were slurried in dichloromethane (25 ml), and triethylamine (0.43 ml, 3.1 mmol) was added. Excess ammonia solution in ethanol (2M) was added and the resulting mixture was stirred for 1 hour. The solvent removed under reduced pressure and the residue was taken up in water. It was basified by adding 1M sodium hydroxide solution, and then extracted with ethyl acetate, dried over magnesium sulfate and concentrated under vacuum. Chromatography on silica gel with 0-1% methanol in ethyl acetate gave the title compound (0.82 g).

Workup

  1. customThe solvent removed under reduced pressure
  2. additionby adding 1M sodium hydroxide solution
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-355664507435422d85ebb19dc5311ef3
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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