Methanesulfonyl chloride → HCID 69307287, compound

HRID 1852549Notes

Reaction equation

HRID 1852549 reaction equation
[N:1]1([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH:17]3[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]3)[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[N:1]1([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH:17]3[CH2:22][CH2:21][CH2:20][N:19]([S:24]([CH3:23])(=[O:26])=[O:25])[CH2:18]3)[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 69309708HCID 69309708, compound

Product 1

HCID 69307287HCID 69307287, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To DCM (8 mL) was added (4-benzotriazol-1-yl-pyrimidin-2-yl)-piperidin-3-ylamine (0.15 g), methanesulfonyl chloride (35 μL) and TEA (0.285 mL), and the mixture stirred at RT. The product was purified by column chromatography on silica, using 100% DCM to 15% MeOH/DCM, then recrystallized from EtOAc to provide (4-benzotriazol-1-yl-pyrimidin-2-yl)-(1-methanesulfonyl-piperidin-3-yl)-amine. Mp=196.0-197.0° C., 1H nmr (300 MHz, DMSO-d6): δ ppm 1.40-1.76 (m, 2H), 1.78-2.14 (m, 2H), 2.72-2.86 (m, 2H), 2.89 (s, 3H), 3.49 (m, 1H), 3.78 (m, 1H), 4.02 (m, 1H), 7.41 (d, J=5.27 Hz, 1H), 7.58 (t, J=7.35 Hz, 1H), 7.73 (m, 1H), 8.22 (d, J=8.29 Hz, 1H), 8.55 (d, J=5.27 Hz, 1H), 8.88 (d, 1H).

Workup

  1. customThe product was purified by column chromatography on silica
  2. customrecrystallized from EtOAc

Sources & evidence

ORD record
ord-da80a1c2b5b141b89111f68d6d537539
Source dataset
uspto-grants-2015_02
Patent number
US08962622B2

Reaction notes

Loading…