Hydrogen Bromide → HCID 68455069, compound

HRID 2357618Notes

Reaction equation

HRID 2357618 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:36])=[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19]([C:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH:24]=3)=[N:18][N:17]=[CH:16]4)[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.Br>CO.O.ClCCl>[CH:1]1([NH:4][C:5](=[O:6])[C:7]2[CH:8]=[CH:9][C:10]([CH3:36])=[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19]([C:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH:24]=3)=[N:18][N:17]=[CH:16]4)[CH:12]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 260Hydrogen BromideHCID 11848248HCID 11848248, compound

Product 1

HCID 68455069HCID 68455069, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 4-(6-(5-(cyclopropylcarbamoyl)-2-methylphenyl)phthalazin-1-yl)-5,6-dihydropyridine-1(2H)-carboxylate (100 mg, 206 μmol) (Method B) in 2 mL methanol was stirred at RT was treated with 1 mL HBr 48% in H2O. The mixture was stirred for 2 h from 0° C. to RT. The mixture was diluted with 20 mL dichloromethane, washed with 1N NaOH to pH11. The mixture was extracted with dichloromethane (3×20 mL). The combined organics were washed with 20 mL brine, dried over anhydrous Na2SO4, concentrated via vacuum and purified by silica gel chromatography eluting with 10% 2M ammonia methanol/dichloromethane to give the title compound as a pale yellow solid. Found MS (ES+): 385(M+H)+.

Workup

  1. stirringThe mixture was stirred for 2 h from 0° C. to RT
  2. washwashed with 1N NaOH to pH11
  3. extractionThe mixture was extracted with dichloromethane (3×20 mL)
  4. washThe combined organics were washed with 20 mL brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated via vacuum
  7. custompurified by silica gel chromatography
  8. washeluting with 10% 2M ammonia methanol/dichloromethane

Sources & evidence

ORD record
ord-395642e9898941d78f185fe8c1f76125
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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