Triethylamine → HCID 57513831, compound

HRID 2368418Notes

Reaction equation

HRID 2368418 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][C:9]([C:12](=[O:27])[NH:13][C:14]2[S:15][C:16]([CH2:25]O)=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:18]=2)([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=1.CS(Cl)(=O)=O.C(N(CC)CC)C.[C:42]([N:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1)([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43]>ClCCl>[C:45]([O:44][C:42]([N:49]1[CH2:54][CH2:53][N:52]([CH2:25][C:16]2[S:15][C:14]([NH:13][C:12](=[O:27])[C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:29][CH:28]=3)([CH3:11])[CH3:10])=[N:18][C:17]=2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:51][CH2:50]1)=[O:43])([CH3:48])([CH3:46])[CH3:47]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 57513832HCID 57513832, compound

Product 1

HCID 57513831HCID 57513831, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-Fluoro-N-[1-(5-hydroxymethyl-4-phenyl-thiazol-2-ylcarbamoyl)-1-methyl-ethyl]-benzamide (82 mg, 0.20 mmol), MsCl (40 uL) and triethylamine (160 uL) in dichloromethane (3 mL) was stirred at RT for 20 min and concentrated. The residue was taken up in MeCN (5 mL), and N-Boc piperazine (120 mg, 0.644 mmol) and triethylamine (160 uL) were added. The mixture was stirred at RT for 20 min and partitioned between ethyl acetate and aq. K2CO3. The combined organic extract was dried over MgSO4, concentrated and chromatographed to give the title compound. m/z 582.2 (MH+).

Workup

  1. concentrationconcentrated
  2. stirringThe mixture was stirred at RT for 20 min
  3. custompartitioned between ethyl acetate and aq. K2CO3
  4. extractionThe combined organic extract
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated
  7. customchromatographed

Sources & evidence

ORD record
ord-e77589e6e88c42f4a004d04c1ef91b34
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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