Ammonia → HCID 178514018, compound

HRID 2273480Notes

Reaction equation

HRID 2273480 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:15][C:16]([C:18]2[CH:19]=[N:20][C:21]([OH:24])=[N:22][CH:23]=2)=[O:17])[CH2:9][C@@H:10]([OH:14])[C:11](O)=[O:12])=[CH:3][CH:2]=1.C[N:32](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N.CCN(C(C)C)C(C)C>CN(C=O)C.O1CCOCC1>[C:1]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:15][C:16]([C:18]2[CH:23]=[N:22][C:21]([OH:24])=[N:20][CH:19]=2)=[O:17])[CH2:9][C@H:10]([C:11](=[O:12])[NH2:32])[OH:14])=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178523853HCID 178523853, compound

Product 1

HCID 178514018HCID 178514018, compoundYield 13.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

(2R,4R)-5-Biphenyl-4-yl-2-hydroxy-4-[(2-hydroxypyrimidine-5-carbonyl)amino]pentanoic acid (14.5 mg, 35.6 μmol, 1.0 eq.) and HATU (13.5 mg, 35.6 μmol, 1.0 eq.) were combined in DMF (5 mL), and the resulting mixture was stirred for 2 minutes. 0.5 M ammonia in dioxane was added, followed by DIPEA (12.4 μL). The resulting mixture was stirred for 1 hour then dried under vacuum. The product was purified using reverse phase chromatography (10-70% MeCN/H2O; 0.05% TFA over 70 minutes) to yield the title compound (2 mg). MS m/z [M+H]+ calc'd for C22H22N4O4, 407.16. found 407.4.

Workup

  1. stirringThe resulting mixture was stirred for 1 hour
  2. customthen dried under vacuum
  3. customThe product was purified
  4. customphase chromatography (10-70% MeCN/H2O; 0.05% TFA over 70 minutes)

Sources & evidence

ORD record
ord-910d3b4555ba48e29180a879a6ddbecd
Source dataset
uspto-grants-2015_09
Patent number
US09120747B2

Reaction notes

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