Methanol → HCID 68684933, compound

HRID 2234300Notes

Reaction equation

HRID 2234300 reaction equation
Cl[C:2]1[N:12]=[C:11]2[C:5]([N:6]([CH3:22])[C:7](=[O:21])[CH2:8][CH2:9][N:10]2[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:4][N:3]=1.[NH2:23][C:24]1[CH:39]=[CH:38][C:27]([C:28]([NH:30][CH:31]2[CH2:36][CH2:35]N(C)[CH2:33][CH2:32]2)=[O:29])=[CH:26][C:25]=1[O:40][CH3:41].O.[C:43]1(C)C=CC(S(O)(=O)=O)=CC=1.CO>CC(O)C>[CH:31]1([NH:30][C:28](=[O:29])[C:27]2[CH:38]=[CH:39][C:24]([NH:23][C:2]3[N:12]=[C:11]4[C:5]([N:6]([CH3:22])[C:7](=[O:21])[CH2:8][CH2:9][N:10]4[CH2:13][CH2:14][N:15]4[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]4)=[CH:4][N:3]=3)=[C:25]([O:40][CH3:41])[CH:26]=2)[CH2:32][CH2:33][CH2:43][CH2:35][CH2:36]1

Participants

6

Reactant 4

HCID 887MethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 115290634-Amino-3-methoxy-n-(1-methylpiperidin-4-yl)benzamideHCID 86617555HCID 86617555, compound2×

Product 1

HCID 68684933HCID 68684933, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

10-chloro-6-methyl-2-[2-(1-piperidyl)ethyl]-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one (Intermediate 159; 90 mg, 0.28 mmol), 4-amino-3-methoxy-N-(1-methyl-4-piperidyl)benzamide (WO06/018220; 83 mg, 0.34 mmol) and p-toluenesulphonic acid monohydrate (107 mg, 0.56 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 (40 mg, 27%).

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-310630c116034bd0a7de7097aa610c62
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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