3,5-Difluorobenzenesulfonyl chloride → HCID 68902717, compound

HRID 736335Notes

Reaction equation

HRID 736335 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[NH2:13][C:14]1[C:15]2[C:22]([C:23]([C:25]3[CH:26]=[N:27][CH:28]=[C:29]([NH2:31])[CH:30]=3)=[O:24])=[CH:21][N:20]([CH:32]([CH3:34])[CH3:33])[C:16]=2[N:17]=[CH:18][N:19]=1>N1C=CC=CC=1>[NH2:13][C:14]1[C:15]2[C:22]([C:23]([C:25]3[CH:30]=[C:29]([NH:31][S:9]([C:4]4[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=4)(=[O:11])=[O:10])[CH:28]=[N:27][CH:26]=3)=[O:24])=[CH:21][N:20]([CH:32]([CH3:34])[CH3:33])[C:16]=2[N:17]=[CH:18][N:19]=1

Participants

4

Reactant 2

HCID 27740583,5-Difluorobenzenesulfonyl chlorideHCID 68903795(4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(5-amino-pyridin-3-yl)-methanone

Product 1

HCID 68902717HCID 68902717, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

3,5-Difluoro-benzenesulfonyl chloride (19.7 mg, 0.093 mmol) was added to a solution of (4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(5-amino-pyridin-3-yl)-methanone (25 mg, 0.084 mmol) in pyridine (0.7 mL). The resulting solution was heated to 40° C. for 16 h. The reaction mixture was concentrated in vacuo and the residue dissolved in DMSO (2 mL) and purified using reverse phase preparative HPLC to furnish the title compound as a white solid. MS: 473.2 (MH+); HPLC Rf: 4.91 min. (HPLC method 4).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in DMSO (2 mL)
  3. custompurified

Sources & evidence

ORD record
ord-9400d23e42d84e22b08be6a75b7b772a
Source dataset
uspto-grants-2009_09
Patent number
US07595325B2

Reaction notes

Loading…