Methanesulfonyl chloride → HCID 178462818, compound

HRID 1884910Notes

Reaction equation

HRID 1884910 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:17]=[C:16]([NH:18][C@H:19]3[CH2:24][CH2:23][C@H:22]([OH:25])[CH2:21][CH2:20]3)[N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[CH2:26][CH3:27])=[CH:4][CH:3]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl>[CH2:26]([N:13]1[CH:12]=[N:11][C:10]2[C:14]1=[N:15][C:16]([NH:18][C@H:19]1[CH2:20][CH2:21][C@H:22]([OH:25])[CH2:23][CH2:24]1)=[N:17][C:9]=2[NH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:3][CH:4]=1)[CH3:27]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 178462815HCID 178462815, compound

Product 1

HCID 178462818HCID 178462818, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

trans-4-[6-(4-amino-phenylamino)-9-ethyl-9H-purin-2-yl-amino]-cyclohexanol (100 mg, 0.272 mmol) is suspended in 1 ml dichloromethane and treated with 22 μl (0.272 mmol) methanesulfonyl chloride. The reaction mixture is stirred at RT for 48 h. The crude product is recovered by filtration and purified by chromatography on silica gel (CH2Cl2/MeOH 95:5). N-{4-[9-ethyl-2-(trans-4-hydroxy-cyclohexylamino)-9H-purin-6-yl-amino]-phenyl}-methane-sulfonamide is obtained as an amorphous material, 43 mg (36%); MS [M+H]+444; HPLC (System h) tR=4.63 min.

Workup

  1. filtrationThe crude product is recovered by filtration
  2. custompurified by chromatography on silica gel (CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-20662507837d4f0983614cccaf3beca1
Source dataset
uspto-grants-2004_07
Patent number
US06767906B2

Reaction notes

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