Diisopropylethylamine → HCID 74316295, compound

HRID 737159Notes

Reaction equation

HRID 737159 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]([OH:18])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[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.Br.[NH2:53][C:54]1[S:55][C:56]([Br:59])=[CH:57][N:58]=1>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16](=[O:18])[NH:53][C:54]1[S:55][C:56]([Br:59])=[CH:57][N:58]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 101987Benzyloxycarbonyl-L-prolineHCID 27238485-Bromothiazol-2-amine monohydrobromideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 74316295HCID 74316295, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-Pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (1.44 g, 5.78 mmol), HATU (2.2 g, 5.78 mmol), and DIEA (1.5 mL, 11.6 mmol)in DMF (30 mL) was stirred at room temperature for 1 h. The 2-Amino-5-bromo-thiazole hydrobromide salt (FW=259.95, 1.0 g, 3.85 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: 504.1 (M+H+).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 20 h
  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-b260564e48994d71aaf9131c28b5eec8
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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