Hydrochloric Acid → (+/-)-4-Oxo-2-pyridin-4-yl-9-[(1,2,3,4-tetrahydro-isoquinoline-7-carbonyl)-amino]-5,6,8,9-tetrahydro-4H-1,4a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester

HRID 1890404Notes

Reaction equation

HRID 1890404 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([NH:13][C:14]([C:16]2[CH:25]=[C:24]3[C:19]([CH2:20][CH2:21][N:22](C(OC(C)(C)C)=O)[CH2:23]3)=[CH:18][CH:17]=2)=[O:15])[C:10]2=[N:33][C:34]([C:38]3[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=3)=[CH:35][C:36](=[O:37])[N:9]2[CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl>ClCCl>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([NH:13][C:14]([C:16]2[CH:25]=[C:24]3[C:19]([CH2:20][CH2:21][NH:22][CH2:23]3)=[CH:18][CH:17]=2)=[O:15])[C:10]2=[N:33][C:34]([C:38]3[CH:39]=[CH:40][N:41]=[CH:42][CH:43]=3)=[CH:35][C:36](=[O:37])[N:9]2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 44159005HCID 44159005, compound

Product 1

HCID 44159256(+/-)-4-Oxo-2-pyridin-4-yl-9-[(1,2,3,4-tetrahydro-isoquinoline-7-carbonyl)-amino]-5,6,8,9-tetrahydro-4H-1,4a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl esterYield 1,186.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.0265 g (0. mmol) of (+/−)-9-[(2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-isoquinoline-7-carbonyl)-amino]-4-oxo-2-pyridin-4-yl-5,6,8,9-tetrahydro-4H-1,4a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester (example 5) dissolved in 1 mL of dichloromethane was added 1.13 mL (4.50 mmol) of hydrochloric acid (4M in dioxane). The resulting mixture was stirred at room temperature for 16 hours. The resulting residue was filtered, washed with dichloromethane and isopropylether to afford 0.261 g (100%) of the pure product as a white powder.

Workup

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

Sources & evidence

ORD record
ord-2abe86c3552d424dafa1ef63fbac1e65
Source dataset
uspto-grants-2013_08
Patent number
US08507475B2

Reaction notes

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