1-Methylpiperazine → HCID 178491851, compound

HRID 1371758Notes

Reaction equation

HRID 1371758 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:19])[C:9]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]([F:17])[C:10]=2[F:18])=[CH:6][N:5]=[C:4]([NH:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([NH:27][S:28]([CH2:31][CH2:32][CH2:33]Cl)(=[O:30])=[O:29])[CH2:23][CH2:22]2)[N:3]=1.[CH3:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>O1CCCC1>[NH2:1][C:2]1[C:7]([C:8](=[O:19])[C:9]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]([F:17])[C:10]=2[F:18])=[CH:6][N:5]=[C:4]([NH:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([NH:27][S:28]([CH2:31][CH2:32][CH2:33][N:39]3[CH2:40][CH2:41][N:36]([CH3:35])[CH2:37][CH2:38]3)(=[O:30])=[O:29])[CH2:23][CH2:22]2)[N:3]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 178491850HCID 178491850, compound

Product 1

HCID 178491851HCID 178491851, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-chloro-propane-1-sulfonic acid [4-[4-amino-5-(2,3-difluoro-6-methoxy-benzoyl)-pyrimidin-2-ylamino]-cyclohexyl]-amide (104 mg, 0.20 mmol, Example 293) in tetrahydrofuran (5 mL), N-methylpiperizine (100 mg, 1 mmol, Aldrich,) was added and the mixture was heated at reflux for 24 hours. The reaction was quenched with water and the mixture was extracted with ethyl acetate (3×5 mL). The extracts were combined and dried with sodium sulfate and concentrated. The residue was chromatographed (8% 9N ammonia in methanol/dichloromethane) to give a pale yellow solid. 85 mg, 73%. MS (ES) MH+=582.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 24 hours
  3. customThe reaction was quenched with water
  4. extractionthe mixture was extracted with ethyl acetate (3×5 mL)
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed (8% 9N ammonia in methanol/dichloromethane)
  8. customto give a pale yellow solid

Sources & evidence

ORD record
ord-dd9226d04e904651be5f6d7ffdc8c290
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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