Methanesulfonyl chloride → HCID 10120817, compound

HRID 1282008Notes

Reaction equation

HRID 1282008 reaction equation
[Cl:1][C:2]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:3]=1[CH2:4][N:5]1[CH2:9][C@H:8]([C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[C@@H:7]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][O:23][CH2:24][CH2:25][CH2:26][NH2:27])[CH2:18][CH2:17]2)[CH2:6]1.[CH3:33][S:34](Cl)(=[O:36])=[O:35].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:3]=1[CH2:4][N:5]1[CH2:9][C@H:8]([C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[C@@H:7]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][O:23][CH2:24][CH2:25][CH2:26][NH:27][S:34]([CH3:33])(=[O:36])=[O:35])[CH2:18][CH2:17]2)[CH2:6]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 10206976HCID 10206976, compound

Product 1

HCID 10120817HCID 10120817, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.030 g (0.06 mmol) of 1-(2,4-dichlorobenzyl)-3-(S)-(4-(3-aminopropyloxymethyl)piperidinylmethyl)-4-(S)-(3-thienyl)pyrrolidine, 0.02 mL (0.24 mmol) of methanesulfonyl chloride, and 0.03 mL (0.15 mmol) of diisopropylethyl amine in 0.5 mL of CH2Cl2 was stirred at rt for 18 h. The reaction mixture was concentrated and the residue was purified by chromatography (silica, CH2Cl2:methanol, 95:5) to give the title compound. Mass Spectrum (ESI) m/e=574 (M+1 35Cl, 35Cl), 576 (M+1 35Cl, 37Cl), and 578 (M+1 37Cl, 37Cl). [a]D=+11.0 (c=0.815, CHCl3).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography (silica, CH2Cl2:methanol, 95:5)

Sources & evidence

ORD record
ord-a5bc1da29ad64f75865fa7d6834d86cb
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

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