Citric Acid → HCID 67141017, compound

HRID 1445071Notes

Reaction equation

HRID 1445071 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 t, 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-f2c9505a60b846e190122d24ab0a110b
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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