Hydrochloric Acid → HCID 131727574, compound

HRID 2100630Notes

Reaction equation

HRID 2100630 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:9](=[O:14])[N:8]([CH2:15][CH2:16][O:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[C@@H:7]3[CH2:24][N:25](C(OC(C)(C)C)=O)[CH2:26][C@H:6]3[C:5]=2[CH:4]=1)[CH3:2].[ClH:34]>CCOCC.O>[ClH:34].[ClH:34].[CH2:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:9](=[O:14])[N:8]([CH2:15][CH2:16][O:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[C@@H:7]3[CH2:24][NH:25][CH2:26][C@H:6]3[C:5]=2[CH:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 91580172HCID 91580172, compound

Product 1

HCID 131727574HCID 131727574, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of (±)-trans tert-butyl 8-ethyl-6-methyl-5-oxo-4-(2-(pyridin-3-yloxy)ethyl)-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate (20 mg, 0.044 mmol) in 4 mL of ether was added 1 mL of 12 N HCl. The reaction was stirred vigorously for 5 min and then was diluted with 5 mL of water. The reaction was washed with ethyl acetate twice to remove the triphenylphosphine impurity. The aqueous layer was concentrated in vacuo, taken up in water, filtered and lyophilized to afford 8 mg (44%) of the title compound of Example 89 as a light tan powder. 1H NMR (DMSO-D6): δ 9.96-9.90 (broad m, 3H), 8.71 (s, 1H), 8.31-8.26 (m, 1H), 8.03-7.98 (m, 1H), 7.69-7.63 (m, 1H), 6.99 (s, 1H), 6.83 (s, 1H), 4.28-4.23 (m, 1H), 4.20-4.15 (m, 1H), 4.07-4.00 (m, 1H), 3.90-3.84 3.82-3.70 (overlapping m, 2H), 3.55-3.49 (m, 1H), 3.46-3.39 (m, 1H), 3.33-3.26 (m, 1H), 3.21-3.14 (m, 1H), 2.50 (q, 2H, J=7.5 Hz), 2.46 (s, 3H), 1.08 (t, 3H, J=7.7 Hz). LRMS (ESI): 352.1 (M+H)+.

Workup

  1. washThe reaction was washed with ethyl acetate twice
  2. customto remove the triphenylphosphine impurity
  3. concentrationThe aqueous layer was concentrated in vacuo
  4. filtrationfiltered

Sources & evidence

ORD record
ord-fa200008723f4604b101766232070a10
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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