Methanesulfonamide → HCID 58413309, compound

HRID 532288Notes

Reaction equation

HRID 532288 reaction equation
[F:1][CH2:2][CH:3]([O:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[NH:14][C:15]1[C:16]2[C:23]([CH3:24])=[C:22]([C:25](O)=[O:26])[S:21][C:17]=2[N:18]=[CH:19][N:20]=1)[CH2:4][F:5].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>[F:1][CH2:2][CH:3]([O:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[NH:14][C:15]1[C:16]2[C:23]([CH3:24])=[C:22]([C:25]([NH:44][S:41]([CH3:40])(=[O:43])=[O:42])=[O:26])[S:21][C:17]=2[N:18]=[CH:19][N:20]=1)[CH2:4][F:5]

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58413241HCID 58413241, compound

Product 1

HCID 58413309HCID 58413309, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-(2-(1,3-Difluoropropan-2-yloxy)-4-fluorophenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylic acid (197 mg), 4-dimethylaminopyridine (76 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (125 mg) was dissolved in dichloromethane (20 ml). Methanesulfonamide (59.5 mg) was added and the reaction was stirred at room temperature for about 24 h. The mixture was washed with a KHSO4 solution. The organic layer was separated, dried and concentrated in vacuo. The residue was purified by chromatography (dichloromethane: methanol: NH3 80:20:1). The fractions were collected and triturated with diisopropyl ether.

Workup

  1. washThe mixture was washed with a KHSO4 solution
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (dichloromethane: methanol: NH3 80:20:1)
  6. customThe fractions were collected
  7. customtriturated with diisopropyl ether

Sources & evidence

ORD record
ord-c1196e669b3e4ae89ff805d18611c822
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

Loading…