Hydrochloric Acid → HCID 5258522, compound

HRID 2100567Notes

Reaction equation

HRID 2100567 reaction equation
[O:1]=[C:2]1[C:11]2[C:10]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:8]=[CH:7][C:6]=2[C@H]2CN(C(OC(C)(C)C)=O)[CH2:18][C@H:4]2[NH:3]1.Cl.O1CCO[CH2:29][CH2:28]1>C(OCC)C>[CH2:28]([N:3]([CH2:4][CH3:18])[C:2](=[O:1])[C:11]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[C:12]([F:13])([F:14])[F:15])[CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-Dioxane2×HCID 69056519HCID 69056519, compound

Product 1

HCID 5258522HCID 5258522, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (±)-cis-tert-butyl 5-oxo-6-(trifluoromethyl)-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate (50 mg, 0.14 mmol) in 1 mL of 1,4-dioxane was added 4 mL of 4 N HCl in dioxane. The reaction was allowed to stir for 4 h and then was diluted with diethyl ether. A solid slowly settled out of solution. The solvents were decanted and the remaining solid was triturated twice with diethyl ether and dried in vacuo to afford 35 mg (85%) of the title compound of Example 1 as an off-white solid. 1H NMR (DMSO-D6): δ 9.8 (broad s, 1H), 9.6 (broad s, 1H), 8.15 (s, 1H), 7.86 (d, 1H, J=7.1 Hz), 7.78-7.70 (m, 2H), 4.40-4.38 (m, 1H), 3.75-3.67 (m, 2H), 3.55-3.52 (m, 1H), 3.45-3.37 (m, 1H), 3.10-3.05 (m, 1H). LRMS (ESI): 257.16 (M+H)+.

Workup

  1. customThe solvents were decanted
  2. customthe remaining solid was triturated twice with diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-92713d8a99844a20be18e9a9091fe96d
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

Loading…