Diisopropylethylamine → HCID 73052913, compound

HRID 2275495Notes

Reaction equation

HRID 2275495 reaction equation
[CH3:1][O:2][N:3]1[CH:7]=[C:6]([C:8]([OH:10])=O)[N:5]=[N:4]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:35][C@H:36]([CH2:45][C:46]1[CH:51]=[CH:50][C:49]([C:52]2[CH:57]=[C:56]([Cl:58])[CH:55]=[CH:54][C:53]=2[F:59])=[CH:48][CH:47]=1)[CH2:37][C@:38]([CH2:43][OH:44])([CH3:42])[C:39]([OH:41])=[O:40].CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:58][C:56]1[CH:55]=[CH:54][C:53]([F:59])=[C:52]([C:49]2[CH:48]=[CH:47][C:46]([CH2:45][C@@H:36]([NH:35][C:8]([C:6]3[N:5]=[N:4][N:3]([O:2][CH3:1])[CH:7]=3)=[O:10])[CH2:37][C@:38]([CH2:43][OH:44])([CH3:42])[C:39]([OH:41])=[O:40])=[CH:51][CH:50]=2)[CH:57]=1

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 89964351HCID 89964351, compoundHCID 89964407HCID 89964407, compound

Product 1

HCID 73052913HCID 73052913, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Methoxy-1H-[1,2,3]triazole-4-carboxylic acid (4.3 mg, 30 μmol) and HATU (11.4 mg, 30 μmol) were combined in DMF (1 mL) and stirred at room temperature for 15 minutes. (2S,4R)-4-amino-5-(5′-chloro-2′-fluorobiphenyl-4-yl)-2-hydroxymethyl-2-methylpentanoic acid (10 mg, 27 μmol) and DIPEA (14 μL, 82 μmol) were added, and the resulting mixture was stirred for 15 minutes at room temperature. The solvent was removed in vacuo and the residue was purified by preparative HPLC to yield the title compound (1.1 mg). MS m/z [M+H]+ calc'd for C23H24ClFN4O5, 491.14. found 491.2.

Workup

  1. stirringthe resulting mixture was stirred for 15 minutes at room temperature
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-f092cf953f254993ac74b0dc02342e92
Source dataset
uspto-grants-2015_09
Patent number
US09126956B2

Reaction notes

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