Ammonia → HCID 59596671, compound

HRID 2264816Notes

Reaction equation

HRID 2264816 reaction equation
CC(OC([NH:8][C@@H:9]([CH2:14][C:15]#[C:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])=[CH:19][CH:18]=1)[C:10]([O:12][CH3:13])=[O:11])=O)(C)C.N>C(Cl)Cl.O>[NH2:8][C@@H:9]([CH2:14][C:15]#[C:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])=[CH:19][CH:18]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 59596674HCID 59596674, compound

Product 1

HCID 59596671HCID 59596671, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of methyl (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-(4-{[(2-fluorophenyl)methyl]amino}phenyl)-4-pentynoate (D65, 192 mg, 0.450 mmol) in DCM containing 5% TFA (10.5 ml) was stirred at room temperature for 4.5 h. Then 28% NH3 in water was added and the mixture was extracted with DCM. The combined organic layers were dried (Na2SO4), filtered and evaporated to afford the title compound (132 mg). The crude product was used unpurified in the next step. UPLC: 0.56 min, MS: (ES/+) m/z: 327 [MH]+, C19H19FN2O2 requires 326.

Workup

  1. extractionthe mixture was extracted with DCM
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-333b723a9ae144d3a1c7d2b9abc09990
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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