4-Chlorobenzoic Acid → 2-{4-[4-(4-Chloro-benzoylamino)-phenyl]-thiazol-2-ylcarbamoyl}-pyrrolidine-1-carboxylic acid benzyl ester

HRID 737154Notes

Reaction equation

HRID 737154 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:44]([O:51][C:52]([N:54]1[CH2:58][CH2:57][CH2:56][C@H:55]1[C:59](=[O:73])[NH:60][C:61]1[S:62][CH:63]=[C:64]([C:66]2[CH:71]=[CH:70][C:69]([NH2:72])=[CH:68][CH:67]=2)[N:65]=1)=[O:53])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>CN(C=O)C>[CH2:44]([O:51][C:52]([N:54]1[CH2:58][CH2:57][CH2:56][CH:55]1[C:59](=[O:73])[NH:60][C:61]1[S:62][CH:63]=[C:64]([C:66]2[CH:67]=[CH:68][C:69]([NH:72][C:6](=[O:8])[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)=[CH:70][CH:71]=2)[N:65]=1)=[O:53])[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

6

Reactant 4

HCID 63184-Chlorobenzoic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86616427(S)-2-[4-(4-Amino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 765827522-{4-[4-(4-Chloro-benzoylamino)-phenyl]-thiazol-2-ylcarbamoyl}-pyrrolidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-Chlorobenzoic acid (0.017 g, 0.11 mmol), HATU (0.042 g, 0.11 mmol), and DIEA 0.09 mL, 0.67 mmol) in DMF (2 mL) was stirred at room temperature for 1 h. (S)-2-[4-(4-Amino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (FW=422.5096 , 0.029 g, 0.054 mmol) was added. The reaction mixture was stirred at room temperature for 20 h. The mixture was filtered to afford the crude product. The mixture was filtered and separated by reverse phase HPLC (20-100% of buffer B; buffer A: water containing 0.1% TFA; buffer B: MeCN containing 0.1 TFA). The combined fraction was evaporated to dryness to furnish the desired product. MS: 562.1(M+H+).

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. customto afford the crude product
  4. filtrationThe mixture was filtered
  5. customseparated by reverse phase HPLC (20-100% of buffer B
  6. customThe combined fraction was evaporated to dryness

Sources & evidence

ORD record
ord-dd3fef89a0bf49e993039ea14286ce05
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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