Diisopropylethylamine → HCID 74316515, compound

HRID 737152Notes

Reaction equation

HRID 737152 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:56]=[C:57]([C:61]2[N:62]=[C:63]([NH2:66])[S:64][CH:65]=2)[CH:58]=[CH:59][CH:60]=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:57]2[CH:58]=[CH:59][CH:60]=[C:55]([N+:52]([O-:54])=[O:53])[CH:56]=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 81531DiisopropylethylamineHCID 101987Benzyloxycarbonyl-L-prolineHCID 6135042-Amino-4-(3-nitrophenyl)thiazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 74316515HCID 74316515, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Z-Pro-OH (1.5 g, 6.15 mmol) and HATU (2.3 g, 6.15 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-(3-nitro-phenyl)-thiazol-2-ylamine (0.9, 4.1 mmol). Reaction mixture was stirred at room temperature overnight. The crude material was purified using reverse phase HPLC to yield 2-[4-(3-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-c5bfd7dbe23a404ea96e5f41a5ae20a4
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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