Hydrogen Bromide → HCID 68454065, compound

HRID 2357620Notes

Reaction equation

HRID 2357620 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]([CH:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)=[N:18][N:17]=[CH:16]4)[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.Br>CO>[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]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[N:18][N:17]=[CH:16]4)[CH:12]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 68452918HCID 68452918, compound

Product 1

HCID 68454065HCID 68454065, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.42 g of Tert-butyl 4-(6-(5-(cyclopropylcarbamoyl)-2-methylphenyl)phthalazin-1-yl)piperidine-1-carboxylate was dissolved in 2 mL methanol, treated with 1 mL 48% HBr at RT and stirred for 1 h. The mixture was quenched with 20 mL 10% Na2CO3 and extracted with dichloromethane (3×50 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with 10% -20% 2 M ammonia methanol/dichloromethane to give the title product as pale yellow solid. Found MS (ES+): 387(M+H)+.

Workup

  1. customThe mixture was quenched with 20 mL 10% Na2CO3
  2. extractionextracted with dichloromethane (3×50 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with 10% -20% 2 M ammonia methanol/dichloromethane

Sources & evidence

ORD record
ord-960197de98f84abeab03802c0fee1ff9
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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