2,2,2-Trichloroethyl chloroformate → HCID 67252263, compound

HRID 2042096Notes

Reaction equation

HRID 2042096 reaction equation
N[C:2]1[N:6]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH2:13][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][CH2:10]3)[N:5]=[C:4]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:3]=1.[C:28](Cl)([O:30][CH2:31][C:32]([Cl:35])([Cl:34])[Cl:33])=[O:29].C([O-])(O)=O.[Na+]>CCOC(C)=O>[C:24]([C:4]1[CH:3]=[C:2]([C:28]([O:30][CH2:31][C:32]([Cl:35])([Cl:34])[Cl:33])=[O:29])[N:6]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH2:13][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH2:11][CH2:10]3)[N:5]=1)([CH3:26])([CH3:27])[CH3:25]

Participants

5

Reactant 3

HCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium BicarbonateHCID 58851701HCID 58851701, compound

Product 1

HCID 67252263HCID 67252263, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of t-butyl 6-(5-amino-3-t-butyl-1H-pyrazol-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (see WO 2006/071940A2, 0.075 g, 0.20 mmol) and Troc-Cl (0.028 ml, 0.21 mmol) in EtOAc (2 ml) was added sat'd. NaHCO3 (0.82 ml, 0.61 mmol). The resulting biphasic solution was stirred at RT overnight. The layers were separated and the aqueous phase was extracted with EtOAc (2×). The combined organic phases were washed with brine (1×), dried (MgSO4) and concentrated in vacuo to give crude t-butyl 6-(3-t-butyl-5-((2,2,2-trichloroethoxy)carbonyl)-1H-pyrazol-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.110 g, 100% yield). 1H NMR (DMSO-d6) δ 9.93 (brs, 1H), 7.29-7.24 (m, 2H), 6.83-6.80 (m, 1H), 6.27 (s, 1H), 4.85 (s, 2H), 4.52 (brs, 2H), 3.57-3.53 (m, 2H), 2.82-2.79 (m, 2H), 1.44 (s, 9H), 1.27 (s, 9H); MS (ESI) m/z: 545.0 (M+H+).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with EtOAc (2×)
  3. washThe combined organic phases were washed with brine (1×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74d7c080b854415a99b89f5857992744
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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