Hydrochloric Acid → HCID 11493483, compound

HRID 2100610Notes

Reaction equation

HRID 2100610 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[C:10]2[C:9](=[O:17])[NH:8][C@H:7]3[CH2:18][N:19](C(OC(C)(C)C)=O)[CH2:20][C@@H:6]3[C:5]=2[CH:4]=1)[CH3:2].[ClH:28]>C(OCC)C>[ClH:28].[CH2:1]([C:3]1[CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[C:10]2[C:9](=[O:17])[NH:8][C@H:7]3[CH2:18][NH:19][CH2:20][C@@H:6]3[C:5]=2[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69057933HCID 69057933, compound

Product 1

HCID 11493483HCID 11493483, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (3aR,9bS)-tert-butyl 8-ethyl-5-oxo-6-(trifluoromethyl)-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate, the first eluting peak from Part H above, (55 mg, 0.14 mmol) in 2 mL of diethyl ether was added 1 mL of 12 N HCl. The resulting mixture was stirred vigorously for 5 min at ambient temperature and then was concentrated and dried in vacuo. The resulting white solid was triturated twice with diethyl ether and dried in vacuo to afford 40 mg (88%) of the title compound of Example 45 as a white solid. 1H NMR (DMSO-D6): δ 9.83 (broad s, 1H), 9.64 (broad s, 1H), 8.89 (s, 1H), 7.66 (s, 1H), 7.43 (s, 1H), 3.95-3.90 (m, 1H), 3.63-3.58 (m, 1H), 3.51-3.45 (m, 1H), 3.34-3.28 (m, 1H), 3.21-3.10 (m, 2H), 2.73 (q, 2H, J=7.7 Hz), 1.21 (t, 3H, J=7.7 Hz). LRMS (ESI): 285.2 (M+H)+.

Workup

  1. concentrationwas concentrated
  2. customdried in vacuo
  3. customThe resulting white solid was triturated twice with diethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-69def50c2cff4f0591ed539ec4735f61
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

Loading…