Hydrochloric Acid → N-((2-(2,6-Dioxopiperidin-3-YL)-1-oxoisoindolin-5-YL)methyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxamide

HRID 63471Notes

Reaction equation

HRID 63471 reaction equation
[O:1]=[C:2]1[CH:7]([N:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([CH2:17][NH:18][C:19]([C:21]4[CH:30]=[C:29]5[C:24]([CH2:25][CH2:26][N:27](C(OC(C)(C)C)=O)[CH2:28]5)=[CH:23][CH:22]=4)=[O:20])[CH:14]=3)[C:9]2=[O:38])[CH2:6][CH2:5][C:4](=[O:39])[NH:3]1.Cl>C(Cl)Cl.C(OCC)C>[O:1]=[C:2]1[CH:7]([N:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([CH2:17][NH:18][C:19]([C:21]4[CH:30]=[C:29]5[C:24]([CH2:25][CH2:26][NH:27][CH2:28]5)=[CH:23][CH:22]=4)=[O:20])[CH:14]=3)[C:9]2=[O:38])[CH2:6][CH2:5][C:4](=[O:39])[NH:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69049348HCID 69049348, compound

Product 1

HCID 44538513N-((2-(2,6-Dioxopiperidin-3-YL)-1-oxoisoindolin-5-YL)methyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 7-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)methylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.53 g, 1.0 mmol) in methylene chloride (100 mL) is treated with HCl (5 mL of a 2N solution in diethyl ether), and stirred at ambient temperature for 48 hours. The mixture is evaporated under vacuum, and triturated in ethyl acetate (10 mL), filtered, and dried under vacuum.

Workup

  1. customThe mixture is evaporated under vacuum
  2. customtriturated in ethyl acetate (10 mL)
  3. filtrationfiltered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-bce9102a0ffa42328b23b67f401d93b2
Source dataset
uspto-grants-2016_09
Patent number
US09447070B2

Reaction notes

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