Water → HCID 9981302, compound

HRID 1371663Notes

Reaction equation

HRID 1371663 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[O:9])=[CH:6][N:5]=[C:4]([NH:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[N:3]=1.C(N(C(C)C)CC)(C)C.[CH3:35][N:36]([CH3:41])[S:37](Cl)(=[O:39])=[O:38].O>O1CCCC1.C(Cl)Cl>[CH3:35][N:36]([CH3:41])[S:37]([N:23]1[CH2:22][CH2:21][CH:20]([NH:19][C:4]2[N:3]=[C:2]([NH2:1])[C:7]([C:8](=[O:9])[C:10]3[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=3[O:17][CH3:18])=[CH:6][N:5]=2)[CH2:25][CH2:24]1)(=[O:39])=[O:38]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 9997668[4-Amino-2-(piperidin-4-ylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone

Product 1

HCID 9981302HCID 9981302, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of [4-amino-2-(piperidin-4-ylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone (300 mg, 0.87 mmol, Example 59) and diisopropylethylamine (2 mL) in tetrahydrofuran (80 mL) was stirred at +5° C. To this was added dropwise dimethylsulfamoyl chloride (320 mg, 2.23 mmol, Aldrich) in methylene chloride (15 mL). The reaction was stirred at room temperature for 2 hours, poured into water and extracted into methylene chloride (2×50 mL). The combined organic extracts were washed with 5% aqueous sodium bicarbonate. The organic solution was dried (Na2SO4) and solvent was removed under vacuum to give a crude solid. Purification was by silica gel chromatography to give 4-[4-amino-5-(5-fluoro-2-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidine-1-sulfonic acid dimethylamide as a white solid. HRMS, observed: 453.1720; Calcd for M+: 453.1715.

Workup

  1. extractionextracted into methylene chloride (2×50 mL)
  2. washThe combined organic extracts were washed with 5% aqueous sodium bicarbonate
  3. dry with materialThe organic solution was dried (Na2SO4) and solvent
  4. customwas removed under vacuum
  5. customto give a crude solid
  6. customPurification

Sources & evidence

ORD record
ord-f3f6bf02a2da4b558e57566c31609258
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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