Diisopropylethylamine → HCID 178472563, compound

HRID 448603Notes

Reaction equation

HRID 448603 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:7]([OH:9])=O)[NH:5][N:6]=1.CN(C(ON1N=N[C:20]2C=CC=N[C:19]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:43][C@H:44]([CH2:52][C:53]1[CH:58]=[CH:57][C:56]([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)=[CH:55][CH:54]=1)[CH2:45][C@@H:46]([CH2:50][OH:51])[C:47]([OH:49])=[O:48]>CN(C=O)C>[CH2:19]([O:48][C:47](=[O:49])[C@H:46]([CH2:50][OH:51])[CH2:45][C@H:44]([NH:43][C:7]([C:4]1[NH:5][N:6]=[C:2]([Cl:1])[N:3]=1)=[O:9])[CH2:52][C:53]1[CH:54]=[CH:55][C:56]([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)=[CH:57][CH:58]=1)[CH3:20]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68181179HCID 68181179, compoundHCID 178524894HCID 178524894, compound

Product 1

HCID 178472563HCID 178472563, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Chloro-2H-1,2,4-triazole-3-carboxylic acid (60.8 mg, 412 μmol, 1.5 eq.) and HATU (157 mg, 412 μmol, 1.5 eq.) were dissolved in DMF (4.0 mL), and the resulting mixture was stirred for 5 minutes at room temperature to yield the activated acid. DIPEA (95.7 μL) and (2S,4S)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-pentanoic acid (HCl salt, 100 mg, 275 μmol, 1.0 eq.) were added to the activated acid and the resulting mixture was stirred for 10 minutes. The reaction was quenched with water and the product dried under vacuum. The dried solid was dissolved in AcOH and purified by preparative HPLC. The clean fractions were combined and lyophilized to yield the title compound (88 mg, 95% purity). MS m/z [M+H]+ calc'd for C23H25ClN4O4, 457.16. found 457.4.

Workup

  1. customto yield the activated acid
  2. stirringthe resulting mixture was stirred for 10 minutes
  3. customThe reaction was quenched with water
  4. customthe product dried under vacuum
  5. dissolutionThe dried solid was dissolved in AcOH
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-9068eff514684f9db3c1c689608861f1
Source dataset
uspto-grants-2013_07
Patent number
US08481044B2

Reaction notes

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