Hydrochloric Acid → N-(4,4-Dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-2-[(pyridazin-4-ylmethyl)-amino]-benzamide

HRID 969693Notes

Reaction equation

HRID 969693 reaction equation
C(OC([N:8]1[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]2[C:10](=[CH:11][C:12]([NH:20][C:21](=[O:36])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:28]=[CH:29][C:30]3[CH:35]=[CH:34][N:33]=[N:32][CH:31]=3)=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.Cl>CCOC(C)=O>[CH3:18][C:16]1([CH3:19])[C:15]2[C:10](=[CH:11][C:12]([NH:20][C:21](=[O:36])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[NH:28][CH2:29][C:30]3[CH:35]=[CH:34][N:33]=[N:32][CH:31]=3)=[CH:13][CH:14]=2)[CH2:9][NH:8][CH2:17]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 695103724,4-Dimethyl-7-{2-[(pyridazin-4-ylmethylene)-amino]-benzoylamino}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 1

HCID 59017472N-(4,4-Dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-2-[(pyridazin-4-ylmethyl)-amino]-benzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4,4-dimethyl-7-{2-[(pyridazin-4-ylmethylene)-amino]-benzoylamino}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (Example 121, Step B, 200 mg, 0.41 mmol) in EtOAC (1 mL). Concentrated HCl in EtOAc (2 mL) was added. The reaction was stirred for 5 h under N2 atmosphere at RT. The solid was filtered off and dissolved in water. The aqueous solution was basified to pH 11-14 using 5 N NaOH. The resulting precipitate was filtered, washed with water and dried under vacuum, to obtain the titled compound as a tan solid. MS (ES+): 388.0 (M+H)+. Calc'd for C23H25N5O: 387.21.

Workup

  1. filtrationThe solid was filtered off
  2. dissolutiondissolved in water
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-108f2d74438b454fae9292122158fb71
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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