Citric Acid → HCID 67141017, compound

HRID 1932357Notes

Reaction equation

HRID 1932357 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([OH:11])=[O:10])([C:5]([OH:7])=[O:6])[OH:4].[CH2:14]([N:17]1[C:21]2=[C:22]([N:26]3[CH2:35][CH2:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:27]3)[N:23]=[CH:24][CH:25]=[C:20]2[C:19]([CH3:36])=[C:18]1[CH3:37])[CH:15]=[CH2:16]>C(OCC)(=O)C>[C:1]([OH:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([OH:11])=[O:10])([C:5]([OH:7])=[O:6])[OH:4].[CH2:14]([N:17]1[C:21]2=[C:22]([N:26]3[CH2:35][CH2:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:27]3)[N:23]=[CH:24][CH:25]=[C:20]2[C:19]([CH3:36])=[C:18]1[CH3:37])[CH:15]=[CH2:16]

Participants

4

Reactant 2

HCID 311Citric AcidHCID 16063927HCID 16063927, compound

Product 1

HCID 67141017HCID 67141017, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The compound prepared in Example 484 was treated with a saturated sodium carbonate solution to obtain 1-allyl-7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine. A solution of citric acid (11.2 μl, 0.09 mmol) in ethyl acetate (0.5 ml) was added to a solution of 1-allyl-7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine (30 mg, 0.08 mmol) in ethyl acetate (3 ml). The reaction mixture was stirred overnight at room temperature. The resulting solid was filtered and then dried to give 17.3 mg of the titled compound as a pink solid.

Workup

  1. filtrationThe resulting solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-b40b31d192744fb4bdcb96a3e890db05
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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