2-Amino-4-(p-nitrophenyl)thiazole → 2-[4-(4-Nitro-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

HRID 737157Notes

Reaction equation

HRID 737157 reaction equation
[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.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.[N+:52]([C:55]1[CH:60]=[CH:59][C:58]([C:61]2[N:62]=[C:63]([NH2:66])[S:64][CH:65]=2)=[CH:57][CH:56]=1)([O-:54])=[O:53]>CN(C=O)C>[CH2:12]([O:11][C:9]([N:1]1[CH2:8][CH2:7][CH2:6][CH:2]1[C:3](=[O:5])[NH:66][C:63]1[S:64][CH:65]=[C:61]([C:58]2[CH:57]=[CH:56][C:55]([N+:52]([O-:54])=[O:53])=[CH:60][CH:59]=2)[N:62]=1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 164202-Amino-4-(p-nitrophenyl)thiazoleHCID 81531DiisopropylethylamineHCID 101987Benzyloxycarbonyl-L-prolineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 765828192-[4-(4-Nitro-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Z-Pro-OH (1.46 g, 5.85 mmol) and HATU (2.2 g, 5.85 mmol) were combined in 30 mL of dry DMF. To this solution was added DIEA(1.5 mL, 8.8 mmol). This solution was stirred at room temperature for 1 hour. To this solution was added 4-(4-nitro-phenyl)-thiazol-2-ylamine (1.0 g, 4.5 mmol). Reaction mixture was stirred at room temperature overnight. The crude material was purified using HPLC to yield 2-[4-(4-Nitro-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester. MS: 453.1 (M+H+).

Workup

  1. customReaction mixture
  2. stirringwas stirred at room temperature overnight
  3. customThe crude material was purified

Sources & evidence

ORD record
ord-ab2146330e3041f2966127c3be1a865b
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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