4-Methylmorpholine → 4-[4-Amino-5-(2,3-difluoro-6-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidine-1-sulfonic Acid acetyl-amide

HRID 1371750Notes

Reaction equation

HRID 1371750 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][CH:21]2[CH2:26][CH2:25][N:24]([S:27]([NH2:30])(=[O:29])=[O:28])[CH2:23][CH2:22]2)[N:3]=1.CN(C1C=CC=CN=1)C.CN1CC[O:44][CH2:43][CH2:42]1>ClCCl.C(OC(=O)C)(=O)C>[C:43]([NH:30][S:27]([N:24]1[CH2:25][CH2:26][CH:21]([NH:20][C:4]2[N:3]=[C:2]([NH2:1])[C:7]([C:8](=[O:19])[C:9]3[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11]([F:17])[C:10]=3[F:18])=[CH:6][N:5]=2)[CH2:22][CH2:23]1)(=[O:28])=[O:29])(=[O:44])[CH3:42]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 218852-DimethylaminopyridineHCID 100720334-[4-Amino-5-(2,3-difluoro-6-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidine-1-sulfonic acid amide

Product 1

HCID 104804674-[4-Amino-5-(2,3-difluoro-6-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidine-1-sulfonic Acid acetyl-amide

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideCatalystHCID 6344DichloromethaneSolvent

Procedure

4-[4-Amino-5-(2,3-difluoro-6-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidine-1-sulfonic acid amide (50 mg, Example 285) in dichloromethane (10 mL), N-methyl morpholine (0.1 mL, Aldrich) and dimethylaminopyridine (1 mg, Aldrich) was chilled in ice and added acetic anhydride (5 drops). The mixture was stirred cold for two hours and quenched with methanol. The mixture was evaporated to dryness and chromatographed on silica gel (dichloromethane, then ethyl acetate). Fractions corresponding to product were combined and crystallized from dichloromethane/ethyl ether to give 45 mg of colorless material, MP 153° C. (dec). MS(ES) MH+ 485

Workup

  1. customquenched with methanol
  2. customThe mixture was evaporated to dryness
  3. customchromatographed on silica gel (dichloromethane
  4. customcrystallized from dichloromethane/ethyl ether

Sources & evidence

ORD record
ord-021286d23e96454981589742266038a1
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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