Methanol → HCID 68684857, compound

HRID 2234299Notes

Reaction equation

HRID 2234299 reaction equation
Cl[C:2]1[N:12]=[C:11]2[C:5]([N:6]([CH3:19])[C:7](=[O:18])[CH2:8][CH2:9][N:10]2[CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])=[CH:4][N:3]=1.[NH2:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([NH:27][CH:28]2[CH2:33][CH2:32]N(C)[CH2:30][CH2:29]2)=[O:26])=[CH:23][C:22]=1[O:37][CH3:38].O.[C:40]1(C)C=CC(S(O)(=O)=O)=CC=1.CO>CC(O)C>[CH:28]1([NH:27][C:25](=[O:26])[C:24]2[CH:35]=[CH:36][C:21]([NH:20][C:2]3[N:12]=[C:11]4[C:5]([N:6]([CH3:19])[C:7](=[O:18])[CH2:8][CH2:9][N:10]4[CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])=[CH:4][N:3]=3)=[C:22]([O:37][CH3:38])[CH:23]=2)[CH2:29][CH2:30][CH2:40][CH2:32][CH2:33]1

Participants

6

Reactant 4

HCID 887MethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 115290634-Amino-3-methoxy-n-(1-methylpiperidin-4-yl)benzamideHCID 86617554HCID 86617554, compound2×

Product 1

HCID 68684857HCID 68684857, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

10-chloro-2-(2-dimethylaminoethyl)-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one (Intermediate 158; 84 mg, 0.30 mmol), 4-amino-3-methoxy-N-(1-methyl-4-piperidyl)benzamide (WO06/018220; 90 mg, 0.36 mmol) and p-toluenesulphonic acid monohydrate (113 mg, 0.60 mmol) were heated together in IPA (4 mL) by microwave irradiation at 150° C. for 20 minutes. The reaction mixture was loaded onto an SCX-2 (5 g) column pre-wet with methanol; the column was washed with methanol and the product eluted with 2M NH3/MeOH. Product containing fractions were combined and evaporated. The resultant material was purified by base modified reverse phase preparative HPLC to yield the title compound as a white solid (59 mg, 40%).

Workup

  1. washthe column was washed with methanol
  2. washthe product eluted with 2M NH3/MeOH
  3. additionProduct containing fractions
  4. customevaporated
  5. customThe resultant material was purified by base modified reverse phase preparative HPLC

Sources & evidence

ORD record
ord-47794f0402844338b23921aae2353829
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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