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

HRID 969686Notes

Reaction equation

HRID 969686 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:39])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[NH:28][C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][N:33]=[CH:34][CH:35]=4)[N:30]=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:39])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[NH:28][C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][N:33]=[CH:34][CH:35]=4)[N:30]=3)=[CH:13][CH:14]=2)[CH2:9][NH:8][CH2:17]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69511258HCID 69511258, compound

Product 1

HCID 59017471N-(4,4-Dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-2-([1,7]naphthyridin-2-ylamino)-benzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4,4-dimethyl-7-[2-([1,7]naphthyridin-2-ylamino)-benzoylamino]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (Step B, 200 mg, 0.38 mmol) in EtOAC (2 mL) was added concentrated HCl in EtOAc (5 mL). The mixture was stirred for 5 h at RT under N2 atmosphere. The solid was filtered off and dissolved in water. The aqueous solution was basified to pH 11-14 using 5N NaOH. The solution was extracted with EtOAc, and the organic layer was dried over Na2SO4. The volatiles were removed under reduced pressure and the crude was purified with flash chromatography (SiO2, 5% MeOH/CH2Cl2) to obtain the desired compound as a white solid. MS (ES+): 424.0 (M+H)+. Calc'd for C26H25N5O-423.51.

Workup

  1. filtrationThe solid was filtered off
  2. dissolutiondissolved in water
  3. extractionThe solution was extracted with EtOAc
  4. dry with materialthe organic layer was dried over Na2SO4
  5. customThe volatiles were removed under reduced pressure
  6. customthe crude was purified with flash chromatography (SiO2, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-a871bcfafb144190b43c04d5eb7726fc
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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