Hydrochloric Acid → HCID 69054150, compound

HRID 2100584Notes

Reaction equation

HRID 2100584 reaction equation
CN[C:3](=[O:30])[CH2:4][N:5]1[C@H:14]2[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][C@@H:13]2[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:25]([F:28])([F:27])[F:26])[C:7]=2[C:6]1=[O:29].Cl.[O:32]1CCOCC1>>[C:21]([O:20][C:18]([N:16]1[CH2:17][C@H:13]2[C@@H:14]([N:5]([CH2:4][C:3]([OH:30])=[O:32])[C:6](=[O:29])[C:7]3[C:8]([C:25]([F:28])([F:26])[F:27])=[CH:9][CH:10]=[CH:11][C:12]=32)[CH2:15]1)=[O:19])([CH3:22])([CH3:24])[CH3:23]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 69056193HCID 69056193, compound

Product 1

HCID 69054150HCID 69054150, compoundYield 80%

Procedure

To a solution of (3aR,9bS)-tert-butyl 4-(2-(methylamino)-2-oxoethyl)-5-oxo-6-(trifluoromethyl)-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate (30 mg, 0.07 mmol) in 4 mL of 1,4-dioxane was added 1 mL of 12N HCl. The resulting solution was stirred at ambient temperature for 1 h and then was concentrated. The residue was azeotroped with toluene and dried in vacuo to afford a foam. This foam was triturated 3× with ether and dried in vacuo to afford 20 mg (80%) of the title compound of Example 19 as a pale yellow powder. 1H NMR (DMSO-D6): δ 9.73 and 9.61 (broad singlets, 2H), 8.08 (m, 1H), 7.86 (d, 1H, J=8.3 Hz), 7.76 (t, 1H, J=7.7 Hz), 7.58 (d, 1H, J=7.2 Hz), 4.12 (s, 2H), 4.02-3.95 (m, 2H), 3.70-3.60 (m, 2H), 3.35-3.25 (m, 2H), 2.60 (d, 3H, J=5.0 Hz). LRMS (ESI): 328.17 (M+H)+.

Workup

  1. concentrationwas concentrated
  2. customThe residue was azeotroped with toluene
  3. customdried in vacuo
  4. customto afford a foam
  5. customThis foam was triturated 3× with ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-ad388c428c9447718c875cd464050652
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

Loading…