Methanesulfonamide → HCID 58413203, compound

HRID 240643Notes

Reaction equation

HRID 240643 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]3[C:17]([CH3:18])=[C:16]([C:19](O)=[O:20])[S:15][C:11]=3[N:12]=[CH:13][N:14]=2)=[C:4]([O:22][C@@H:23]2[CH2:27][CH2:26][O:25][CH2:24]2)[CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.[CH3:40][S:41]([NH2:44])(=[O:43])=[O:42]>CN(C)C1C=CN=CC=1.ClCCl.OS([O-])(=O)=O.[K+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]3[C:17]([CH3:18])=[C:16]([C:19]([NH:44][S:41]([CH3:40])(=[O:43])=[O:42])=[O:20])[S:15][C:11]=3[N:12]=[CH:13][N:14]=2)=[C:4]([O:22][C@@H:23]2[CH2:27][CH2:26][O:25][CH2:24]2)[CH:3]=1

Participants

7

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58413081HCID 58413081, compound

Product 1

HCID 58413203HCID 58413203, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 516920Potassium bisulfateSolvent

Procedure

4-{4-Fluoro-2-[(R)-(tetrahydro-furan-3-yl)oxy]-phenylamino}-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid (150 mg), 4-dimethylaminopyridine (61 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (96 mg) was dissolved in dichloromethane. To this mixture methanesulfonamide (48 mg) was added and the reaction was stirred overnight. The reaction mixture was diluted with KHSO4 The organic layer was separated, dried and concentrated. The residue was purified by silica chromatography (Dichloromethane/MeOH/NH3 10:1:0,1).

Workup

  1. customwas separated
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by silica chromatography (Dichloromethane/MeOH/NH3 10:1:0,1)

Sources & evidence

ORD record
ord-b04cadab3227433f8a203c8f88c59811
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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