Hydrochloric Acid → 1,2,3,4-Tetrahydro-isoquinoline-7-carboxylic acid (4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-7-oxa-1,4-a-diaza-benzocyclohepten-9-yl)-amide hydrochloride

HRID 1886967Notes

Reaction equation

HRID 1886967 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:18](=[O:38])[NH:19][CH:20]3[C:26]4=[N:27][C:28]([C:32]5[CH:37]=[CH:36][N:35]=[CH:34][N:33]=5)=[CH:29][C:30](=[O:31])[N:25]4[CH2:24][CH2:23][O:22][CH2:21]3)=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.[ClH:39]>ClCCl>[ClH:39].[O:31]=[C:30]1[N:25]2[C:26]([CH:20]([NH:19][C:18]([C:12]3[CH:11]=[C:10]4[C:15]([CH2:16][CH2:17][NH:8][CH2:9]4)=[CH:14][CH:13]=3)=[O:38])[CH2:21][O:22][CH2:23][CH2:24]2)=[N:27][C:28]([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][N:33]=2)=[CH:29]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 44159737HCID 44159737, compound

Product 1

HCID 866498491,2,3,4-Tetrahydro-isoquinoline-7-carboxylic acid (4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-7-oxa-1,4-a-diaza-benzocyclohepten-9-yl)-amide hydrochlorideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.049 g (0.10 mmol) of (+/−)-7-(4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-7-oxa-1,4-a-diaza-benzocyclohepten-9-ylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (example 1) dissolved in 0.5 mL of dichloromethane was added 0.24 mL (0.96 mmol) of hydrochloric acid (4M in dioxane). The resulting mixture was stirred at room temperature for 2.5 hours. The resulting residue was filtered, washed with dichloromethane and isopropylether to afford 0.031 g (70%) of the pure product as a yellow powder.

Workup

  1. filtrationThe resulting residue was filtered
  2. washwashed with dichloromethane and isopropylether

Sources & evidence

ORD record
ord-54a47bbc66724967a22e644acfdf4d13
Source dataset
uspto-grants-2013_08
Patent number
US08501728B2

Reaction notes

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