Cesium carbonate → HCID 66920147, compound

HRID 1908620Notes

Reaction equation

HRID 1908620 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:35])[C@@H:13]([NH:20][C:21]([C:23]2[CH:27]=[C:26]([OH:28])[N:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:24]=2)=[O:22])[CH2:14][CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:42]([O:44][C:45]([C:47]1(Br)[CH2:50][CH2:49][CH2:48]1)=[O:46])[CH3:43]>CN(C=O)C.O>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:35])[C@@H:13]([NH:20][C:21]([C:23]2[CH:27]=[C:26]([O:28][C:47]3([C:45]([O:44][CH2:42][CH3:43])=[O:46])[CH2:50][CH2:49][CH2:48]3)[N:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:24]=2)=[O:22])[CH2:14][CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 97595Ethyl 1-bromocyclobutanecarboxylateHCID 178473397HCID 178473397, compound

Product 1

HCID 66920147HCID 66920147, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 100 mg of 4-{(S)-2-[(5-Hydroxy-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-4-methanesulfonyl-butyryl}-piperazine-1-carboxylic acid ethyl ester in 2 ml of DMF, 127 mg of cesium carbonate and 81 mg of 1-Bromo-cyclobutanecarboxylic acid ethyl ester was added and heated to 100° C. for 2 h. Then, the reaction mixture was diluted with water and filtered through a Chem Elut® cartridge by eluting with ethyl acetate. The solvents were removed under reduced pressure. The residue was purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA). The fractions containing the product were evaporated and lyophilized to yield a white solid.

Workup

  1. filtrationfiltered through a Chem Elut® cartridge
  2. washby eluting with ethyl acetate
  3. customThe solvents were removed under reduced pressure
  4. customThe residue was purified by preparative HPLC (
  5. washC18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA)
  6. additionThe fractions containing the product
  7. customwere evaporated
  8. customto yield a white solid

Sources & evidence

ORD record
ord-7d952032bab245c7946c97e720c89996
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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