Methanesulfonyl chloride → HCID 11704228, compound

HRID 2375817Notes

Reaction equation

HRID 2375817 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]3[C:13]4[CH:20]=[C:19]([C:21]5[CH2:22][CH2:23][NH:24][CH2:25][CH:26]=5)[NH:18][C:14]=4[N:15]=[CH:16][N:17]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1.CCN(C(C)C)C(C)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>CN(C=O)C>[NH:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]3[C:13]4[CH:20]=[C:19]([C:21]5[CH2:22][CH2:23][N:24]([S:37]([CH3:36])(=[O:39])=[O:38])[CH2:25][CH:26]=5)[NH:18][C:14]=4[N:15]=[CH:16][N:17]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 11508913HCID 11508913, compound

Product 1

HCID 11704228HCID 11704228, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1H-Indazol-5-yl)-[6-(1,2,3,6-tetrahydro-pyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine hydrochloride (80 mg, 0.217 mmol), Hunigs base (113 μL, 0.653 mmol) and methanesulfonyl chloride (17 μL, 0.2177 mmol) were combined in DMF at rt and stirred overnight. The reaction was concentrated in vacuo and residue purified on silica gel by elution with tetrahydrofuran:dichloromethane (3:2) to yield the title compound as white solid. 1H NMR (d6-DMSO, 400 MHz) 9.4(1H, br. s), 8.4 (1H, s), 8.3(1H,s), 8.0(1H,s), 7.7(1H, d), 7.5(1H, d), 6.8(1H, s), 6.4(1H,s), 3.9(2H, s), 3.4(2H, m), 3.0(3H,s) and 2.6(2H, s); LC/MS: m/z 410 [M+H]+, Rt=2.82 min.

Workup

  1. concentrationThe reaction was concentrated in vacuo and residue
  2. custompurified on silica gel by elution with tetrahydrofuran:dichloromethane (3:2)

Sources & evidence

ORD record
ord-ba6fa51e550d412a85a69f3470e7e9ab
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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