Dimethylformamide → (3-methyl-4-(methyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)methanesulfonyl chloride

HRID 472101Notes

Reaction equation

HRID 472101 reaction equation
[CH3:1][CH:2]1[CH:7]([N:8]([CH3:28])[C:9]2[C:10]3[CH:17]=[CH:16][N:15]([S:18]([C:21]4[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=4)(=[O:20])=[O:19])[C:11]=3[N:12]=[CH:13][N:14]=2)[CH2:6][CH2:5][CH:4]([CH2:29][S:30]([OH:33])(=O)=[O:31])[CH2:3]1.C(Cl)[Cl:35].CN(C=O)C.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:1][CH:2]1[CH:7]([N:8]([CH3:28])[C:9]2[C:10]3[CH:17]=[CH:16][N:15]([S:18]([C:21]4[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=4)(=[O:20])=[O:19])[C:11]=3[N:12]=[CH:13][N:14]=2)[CH2:6][CH2:5][CH:4]([CH2:29][S:30]([Cl:35])(=[O:33])=[O:31])[CH2:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 76743942HCID 76743942, compound

Product 1

HCID 86653967(3-methyl-4-(methyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)methanesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of (3-methyl-4-(methyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)methanesulfonic acid (0.400 g, 0.81 mmol), CH2Cl2 (10 mL), and DMF (50 uL) was treated with thionyl chloride and warmed to 40° C. After 1.5 h, the mixture was cooled, treated with toluene (5 mL) and concentrated. The resulting material was triturated with Et2O and dried to afford (3-methyl-4-(methyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)methanesulfonyl chloride that was used immediately without additional manipulation. MS for C22H27ClN4O4S2 (ESI) (MH)+ m/z=512.

Workup

  1. temperaturethe mixture was cooled
  2. concentrationconcentrated
  3. customThe resulting material was triturated with Et2O
  4. customdried

Sources & evidence

ORD record
ord-91e6744a41d24a1ea2649a4fc7c1b130
Source dataset
uspto-grants-2014_01
Patent number
US08633206B2

Reaction notes

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