Methanesulfonyl chloride → HCID 58173402, compound

HRID 2047124Notes

Reaction equation

HRID 2047124 reaction equation
[Br:1][C:2]1[C:3]([CH:22]2[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]2)=[N:4][C:5]2[N:6]([N:9]=[CH:10][C:11]=2[C:12]2[CH:13]=[N:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:7]=1[NH2:8].CCN(C(C)C)C(C)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>CN(C=O)C>[Br:1][C:2]1[C:3]([CH:22]2[CH2:27][CH2:26][CH2:25][N:24]([S:38]([CH3:37])(=[O:40])=[O:39])[CH2:23]2)=[N:4][C:5]2[N:6]([N:9]=[CH:10][C:11]=2[C:12]2[CH:13]=[N:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:7]=1[NH2:8]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67494420HCID 67494420, compound

Product 1

HCID 58173402HCID 58173402, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-bromo-5-(piperidin-3-yl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine (HCl salt, 46 mg, 0.10 mmol) in DMF (2.0 mL) was added DIEA (0.10 mL, 0.30 mmol) and methylsulfonyl chloride (14 mg, 0.12 mmol). The reaction mixture was stirred at rt for 3 h and concentrated in vacuo. The residue was purified by prep-LC to give the title compound. LC/MS RT=2.49 min. Mass calculated for, M+H 486.05, observed 389.17.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by prep-LC

Sources & evidence

ORD record
ord-248d632d22da479f8481b8a1301aa313
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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