Methanesulfonyl chloride → 2-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-{[(methylsulfonyl)amino]methyl}-1,3-thiazole-5-carboxylic acid

HRID 2234013Notes

Reaction equation

HRID 2234013 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]=[C:5]([N:13]2[CH2:18][CH2:17][CH:16]([NH:19][C:20]([C:22]3[NH:23][C:24]([CH3:29])=[C:25]([Cl:28])[C:26]=3[Cl:27])=[O:21])[CH2:15][CH2:14]2)[S:6][C:7]=1[C:8]([O:10]CC)=[O:9].[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[Cl:27][C:26]1[C:25]([Cl:28])=[C:24]([CH3:29])[NH:23][C:22]=1[C:20]([NH:19][CH:16]1[CH2:15][CH2:14][N:13]([C:5]2[S:6][C:7]([C:8]([OH:10])=[O:9])=[C:3]([CH2:2][NH:1][S:31]([CH3:30])(=[O:33])=[O:32])[N:4]=2)[CH2:18][CH2:17]1)=[O:21]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68582554Ethyl 4-(aminomethyl)-2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylate

Product 1

HCID 685799812-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-4-{[(methylsulfonyl)amino]methyl}-1,3-thiazole-5-carboxylic acidYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 4-(aminomethyl)-2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylate (Example 246; 312 mg, 0.677 mmol) was dissolved in DCM and methanesulfonyl chloride (65 μl; 0.844 mmol) was added slowly. The reaction was stirred at room temperature for 16 h, diluted with DCM, washed well with water dried over Na2SO4 and concentrated in vacuo to give the title compound as a light brown thick oil (350 mg)-(LCMS (ES) MH+: 538). The ethyl ester product was hydrolysed with lithium hydroxide/THF in a manner analogous to Example 31 to give the title compound (30 mg).

Workup

  1. washwashed well with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-557ebf8d3e534f44bb28c59a655b93bf
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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