Trifluoroacetic acid → HCID 131736784, compound

HRID 1486330Notes

Reaction equation

HRID 1486330 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:3]=1[CH2:4][O:5][C:6]1[N:11]2[N:12]=[C:13]([CH3:18])[C:14]([C:15](O)=[O:16])=[C:10]2[CH:9]=[C:8]([CH3:19])[CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.C(O)(=O)C.[NH2:62][C@H:63]([C:66]1[O:70][C:69]([C@@H:71]([NH:75][C:76](=[O:82])[O:77][C:78]([CH3:81])([CH3:80])[CH3:79])[CH:72]([CH3:74])[CH3:73])=[N:68][N:67]=1)[CH2:64][OH:65].[C:83]([OH:89])([C:85]([F:88])([F:87])[F:86])=[O:84]>CN(C=O)C.C(#N)C.O>[F:86][C:85]([F:88])([F:87])[C:83]([OH:89])=[O:84].[F:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:2]([F:1])[C:3]=1[CH2:4][O:5][C:6]1[N:11]2[N:12]=[C:13]([CH3:18])[C:14]([C:15]([NH:62][C@H:63]([C:66]3[O:70][C:69]([C@@H:71]([NH:75][C:76](=[O:82])[O:77][C:78]([CH3:79])([CH3:81])[CH3:80])[CH:72]([CH3:73])[CH3:74])=[N:68][N:67]=3)[CH2:64][OH:65])=[O:16])=[C:10]2[CH:9]=[C:8]([CH3:19])[CH:7]=1

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117859510HCID 117859510, compoundHCID 131736785tert-butyl [(1S)-1-{5-[(1S)-1-amino-2-hydroxyethyl]-1,3,4-oxadiazol-2-yl}-2-methylpropyl]carbamate acetate

Product 1

HCID 131736784HCID 131736784, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

124 mg (0.37 mmol) of 7-[(2,6-difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid from Example 4A were initially charged together with 184 mg (0.49 mmol) of HATU and 0.52 ml (3.00 mmol) of N,N-diisopropylethylamine in 1.24 ml of DMF, and the mixture was stirred at room temperature for 10 min. Subsequently, 175 mg (0.49 mmol) of tert-butyl [(1S)-1-{5-[(1S)-1-amino-2-hydroxyethyl]-1,3,4-oxadiazol-2-yl}-2-methylpropyl]carbamate acetate from Example 173A were added to the reaction solution and the mixture was stirred at RT for 1 h. Then the mixture was diluted with acetonitrile and water, admixed with TFA and purified by means of preparative HPLC (RP18 column, eluent:acetonitrile/water gradient with addition of 0.1% TFA). 211 mg of the target compound were obtained (73% of theory, 94% purity).

Workup

  1. stirringthe mixture was stirred at RT for 1 h
  2. custompurified by means of preparative HPLC (RP18 column, eluent:acetonitrile/water gradient with addition of 0.1% TFA)

Sources & evidence

ORD record
ord-7218730af0324a3a82939f5b1263a946
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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