4-Carboxy-1,2,3-triazole → HCID 178459157, compound

HRID 535193Notes

Reaction equation

HRID 535193 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[N:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:33]=[C:34]1[CH2:38][CH2:37][CH2:36][N:35]1[CH2:39][CH2:40][O:41][C:42](=[O:63])[C@@:43]([CH2:61][OH:62])([CH3:60])[CH2:44][C@H:45]([NH2:59])[CH2:46][C:47]1[CH:52]=[CH:51][C:50]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[CH:49][CH:48]=1>CN(C=O)C.CCN(C(C)C)C(C)C>[O:33]=[C:34]1[CH2:38][CH2:37][CH2:36][N:35]1[CH2:39][CH2:40][O:41][C:42](=[O:63])[C@@:43]([CH2:61][OH:62])([CH3:60])[CH2:44][C@H:45]([NH:59][C:6]([C:4]1[NH:3][N:2]=[N:1][CH:5]=1)=[O:8])[CH2:46][C:47]1[CH:48]=[CH:49][C:50]([C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)=[CH:51][CH:52]=1

Participants

6

Reactant 3

HCID 1401204-Carboxy-1,2,3-triazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68181273HCID 68181273, compound

Product 1

HCID 178459157HCID 178459157, compoundYield 20,177.1%

Reagents, catalysts & solvents 2

HCID 81531DiisopropylethylamineCatalystHCID 6228DimethylformamideSolvent

Procedure

1,2,3-Triazole-4-carboxylic acid (14 mg, 124 nmol), DIPEA (86.3 mL, 496 nmol) and HATU (47.1 mg, 124 nmol) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. This was then combined with (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid 2-(2-oxo-pyrrolidin-1-yl)-ethyl ester (52.6 mg, 124 nmol). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The product purified by preparative HPLC and lyophilized to yield the title compound (13 mg; purity 95%). MS m/z [M+H]+ calc'd for C28H33N5O5, 520.25. found 520.4.

Workup

  1. stirringThe resulting mixture was stirred for 15 minutes
  2. customthe reaction was quenched with AcOH
  3. customThe product purified by preparative HPLC

Sources & evidence

ORD record
ord-e8c61aa6b68c4831a579f50177445ca7
Source dataset
uspto-grants-2014_10
Patent number
US08853427B2

Reaction notes

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