Hydrochloric Acid → HCID 11694999, compound

HRID 2100577Notes

Reaction equation

HRID 2100577 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:5]2[CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18][C@@H:4]2[NH:3]1.[ClH:26]>O1CCOCC1>[ClH:26].[F:15][C:12]([F:13])([F:14])[C:10]1[C:11]2[C:2](=[O:1])[NH:3][C@H:4]3[CH2:18][NH:17][CH2:16][C@@H:5]3[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69054189HCID 69054189, compound

Product 1

HCID 11694999HCID 11694999, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the first eluting peak, (3aR,9bS)-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 4 mL of dioxane was added 1 mL of 12 N 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 25 mg (61%) of the title compound of Example 13 as an off-white powder. 1H NMR (DMSO-D6): δ 9.8 (broad s, 1H), 9.6 (broad s, 1H), 9.00 (s, 1H), 7.83 (d, 1H, J=8.2 Hz), 7.73 (t, 1H, J=7.7 Hz), 7.58 (d, 1H, J=7.7 Hz), 3.94-3.90 (m, 1H), 3.67-3.60 (m, 1H), 3.55-3.50 (m, 1H), 3.37-3.32 (m, 1H), 3.20-3.10 (m, 2H). LRMS (ESI): 257.16 (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-02135622e5eb43668a9719f263705261
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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