Triethylamine → HCID 58042847, compound

HRID 564191Notes

Reaction equation

HRID 564191 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]2[S:18][C:19]([CH2:22]O)=[CH:20][CH:21]=2)[C:11](=[O:24])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([N:27](CC)[CH2:28][CH3:29])[CH3:26].CS(Cl)(=O)=O.N1CCCC1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]2[S:18][C:19]([CH2:22][N:27]3[CH2:28][CH2:29][CH2:26][CH2:25]3)=[CH:20][CH:21]=2)[C:11](=[O:24])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 31297Methanesulfonyl chlorideHCID 58042873HCID 58042873, compound

Product 1

HCID 58042847HCID 58042847, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 200 mg (0.59 mmol) 4-benzyloxy-1-[2-(5-hydroxymethyl-thiophen-2-yl)-ethyl]-1H-pyridin-2-one (preparation 11d) in 8.0 mL DCM is added 245 μL (1.76 mmol) triethylamine and subsequently 91 μL (1.17 mmol) methanesulfonyl chloride at RT. The reaction mixture is stirred 1 h at RT and 98 μL (1.17 mmol) pyrrolidine is added. The mixture is stirred overnight at RT and is directly transferred to a reverse HPLC for purification (Zorbax stable bond, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90).

Workup

  1. stirringThe mixture is stirred overnight at RT
  2. customis directly transferred to a reverse HPLC for purification (Zorbax stable bond, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90)

Sources & evidence

ORD record
ord-c8752caf93cf4d64a37d7f10398a50a1
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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