Trimethyl orthoformate → HCID 10205642, compound

HRID 1611655Notes

Reaction equation

HRID 1611655 reaction equation
[NH2:1][C:2]1[CH:29]=[C:28]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:27]=[CH:26][C:3]=1[NH:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7][CH2:6]1.[CH:34](OC)(OC)OC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:33][S:30]([C:28]1[CH:27]=[CH:26][C:3]2[N:4]([CH:5]3[CH2:6][CH2:7][N:8]([CH2:11][CH2:12][CH:13]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:9][CH2:10]3)[CH:34]=[N:1][C:2]=2[CH:29]=1)(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 22254652HCID 22254652, compound

Product 1

HCID 10205642HCID 10205642, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-amino-4-methanesulphonyl-1-N-[-1-(3,3-diphenylpropyl)-piperidin-4-yl]aniline (prepared as described below) (50 mg, 0.1 mmol), trimethyl orthoformate (0.7 ml) and para-toluenesulphonic acid monohydrate (2 mg, 0.11 mmol) was stirred at 100° C. After 2.5 h the mixture was cooled and water (10 ml) was added. The solution was partitioned with EtOAc (2×40 ml) then the organics were combined, dried (MgSO4) and concentrated to give the title compound as an oil (47 mg, 0.1 mmol); MS: 474.

Workup

  1. temperatureAfter 2.5 h the mixture was cooled
  2. customThe solution was partitioned with EtOAc (2×40 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fe0aef211cc345d181df2f4585ada4e2
Source dataset
uspto-grants-2006_01
Patent number
US06989393B2

Reaction notes

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