Diisopropylethylamine → HCID 76582747, compound

HRID 737150Notes

Reaction equation

HRID 737150 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.[NH2:52][C:53]1[S:54][CH:55]=[C:56]([C:58]2[CH:66]=[CH:65][C:61]([C:62]([OH:64])=[O:63])=[CH:60][CH:59]=2)[N:57]=1>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:52][C:53]1[S:54][CH:55]=[C:56]([C:58]2[CH:59]=[CH:60][C:61]([C:62]([OH:64])=[O:63])=[CH:65][CH:66]=2)[N:57]=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 6131794-(2-Amino-1,3-thiazol-4-yl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 76582747HCID 76582747, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Z-ProOH (0.56 g, 2.2 mmol) and HATU (2.2 mmol, 0.83 g) were combined in 35 mL of DMF. To this solution was added DIEA (2.4 mmol, 0.42 mL). This solution was stirred at room temperature for 1 hr. 4-(2-Amino-thiazol-4-yl)-benzoic acid (2.2 mmol, 0.5 g) was then added to the solution. The reaction mixture was stirred at 70° C. overnight. It was brought to room temperature and then evaporated to dryness. The crude was purified using reverse phase HPLC. MS: 452.1 (M+H+)

Workup

  1. stirringThe reaction mixture was stirred at 70° C. overnight
  2. customwas brought to room temperature
  3. customevaporated to dryness
  4. customThe crude was purified

Sources & evidence

ORD record
ord-3e0bfd5ae84a479bbff30a182e608b51
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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