Methanesulfonyl chloride → N-[cis-2-[[5-fluoro-2-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]cyclohexyl]methanesulfonamide

HRID 526944Notes

Reaction equation

HRID 526944 reaction equation
[F:1][C:2]1[C:3]([NH:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]2[NH2:24])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[C:3]([NH:17][C@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]2[NH:24][S:35]([CH3:34])(=[O:37])=[O:36])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 49853546N1-(5-fluoro-2-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)cyclohexane-1,2-diamine2×

Product 1

HCID 68641997N-[cis-2-[[5-fluoro-2-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]cyclohexyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

N1-(5-fluoro-2-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)cyclohexane-1,2-diamine, 16b, (0.009 g, 0.027 mmol) was dissolved in an 8:2 mixture of CH2Cl2/DMF (1 mL) and treated with iPr2NEt (0.019 mL, 0.110 mmol) and methanesulfonyl chloride (0.006 mL, 0.083 mmol). The reaction was stirred at room temperature overnight, concentrated in vacuo and the residue was purified by HPLC with 10%-90% acetonitrile/water with 0.03% TFA to provide compound 337.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by HPLC with 10%-90% acetonitrile/water with 0.03% TFA

Sources & evidence

ORD record
ord-88715c7154c14e65a3fe9c284abeeff1
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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