Methanesulfonamide → HCID 57636073, compound

HRID 216234Notes

Reaction equation

HRID 216234 reaction equation
CCN=C=NCCCN(C)C.Cl.[CH3:13][O:14][C:15]1[N:20]=[C:19]([C:21]2[CH:22]=[C:23]([C:27]3([C:33](O)=[O:34])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:24]=[CH:25][CH:26]=2)[CH:18]=[C:17]([NH:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][C:46]([F:49])([F:48])[F:47])=[CH:41][CH:40]=2)[N:16]=1.[CH3:50][S:51]([NH2:54])(=[O:53])=[O:52]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:13][O:14][C:15]1[N:20]=[C:19]([C:21]2[CH:22]=[C:23]([C:27]3([C:33]([NH:54][S:51]([CH3:50])(=[O:53])=[O:52])=[O:34])[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[CH:24]=[CH:25][CH:26]=2)[CH:18]=[C:17]([NH:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][C:46]([F:49])([F:48])[F:47])=[CH:41][CH:40]=2)[N:16]=1

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86615706HCID 86615706, compound

Product 1

HCID 57636073HCID 57636073, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (39 mg, 0.2 mmol) is added to a stirred ice cold solution of N-[4-(3-{2-methoxy-6-[2-(4-trifluoromethoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenyl)-tetrahydro-pyran-4-carboxylic acid (100 mg, 0.19 mmol), methanesulfonamide (19.3 mg, 0.2 mmol) and 4-dimethylaminopyridine (23.6 mg, 0.19 mmol) in dry DCM under nitrogen. The reaction mixture is stirred overnight at room temperature and concentrated in vacuo. The residue is dissolved in ethyl acetate, washed with 0.1N HCl, brine and water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by chromatography (SiO2 packed column), eluting with ethyl acetate/heptane to afford N-[4-(3-{2-methoxy-6-[2-(4-trifluoromethoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenyl)-tetrahydro-pyran-4-carbonyl]-methanesulfonamide [86 mg, Example 84(a)]. LCMS: RT=2.52 minutes, LCMS: 595 (M+H). IC50=0.7 nM

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed with 0.1N HCl, brine and water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by chromatography (SiO2 packed column)
  8. washeluting with ethyl acetate/heptane

Sources & evidence

ORD record
ord-0ab39f9ac97d4f17a78aba9ec5726de8
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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