Cesium carbonate → HCID 66920241, compound

HRID 1908632Notes

Reaction equation

HRID 1908632 reaction equation
[C:1]([O:5][C:6](=[O:43])[CH2:7][CH2:8][C@H:9]([NH:28][C:29]([C:31]1[CH:35]=[C:34]([OH:36])[N:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[N:32]=1)=[O:30])[C:10](=[O:27])[N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:50][O:51][C:52]([C:54]1[O:55][C:56]([CH2:59]Cl)=[CH:57][CH:58]=1)=[O:53]>CN(C=O)C.C(OCC)(=O)C>[CH3:50][O:51][C:52]([C:54]1[O:55][C:56]([CH2:59][O:36][C:34]2[N:33]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[N:32]=[C:31]([C:29](=[O:30])[NH:28][C@H:9]([C:10]([N:11]3[CH2:12][CH2:13][N:14]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:25])([F:26])[F:24])[CH:18]=4)[CH2:15][CH2:16]3)=[O:27])[CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:43])[CH:35]=2)=[CH:57][CH:58]=1)=[O:53]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 75065Methyl 5-(chloromethyl)-2-furoateHCID 178451022HCID 178451022, compound

Product 1

HCID 66920241HCID 66920241, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

180 mg of (S)-4-[(5-Hydroxy-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-5-oxo-5-[4-(3-trifluoromethyl-phenyl)piperazin-1-yl]-pentanoic acid tert-butyl ester dissolved in 4 ml DMF was treated with 293 mg of cesium carbonate and 78 mg of Methyl-5-(chlormethyl)furan-2-carboxylate. After 3 h at 70° C. the mixture was diluted with ethyl acetate and washed with saturated sodium hydrogen carbonate solution. Drying of the organic layer over sodium sulfate gave crude 5-(5-{(S)-3-tert-Butoxycarbonyl-1-[4-(3-trifluoromethyl-phenyl)-piperazine-1-carbonyl]-propylcarbamoyl}-2-phenyl-2H-pyrazol-3-yloxymethyl)-furan-2-carboxylic acid methyl ester which was used for the subsequent reaction.

Workup

  1. washwashed with saturated sodium hydrogen carbonate solution
  2. dry with materialDrying of the organic layer over sodium sulfate

Sources & evidence

ORD record
ord-7fe6ffd249c245689dcc894808b3ab19
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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