Hydrochloric Acid → HCID 178439312, compound

HRID 2421769Notes

Reaction equation

HRID 2421769 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[N:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:26][N:25]=[N:24][N:23]=3)=[CH:14][CH:15]=2)[N:7]=[C:6]([C:27](O)=[O:28])[CH:5]=1)[CH2:2][CH3:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN(C=O)C.[NH2:68][C@H:69]([CH2:74][C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][C:76]=1[C:81]([F:84])([F:83])[F:82])[CH2:70][C:71]([OH:73])=[O:72].Cl>>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[N:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:23][N:24]=[N:25][N:26]=3)=[CH:14][CH:15]=2)[N:7]=[C:6]([C:27]([NH:68][C@H:69]([CH2:74][C:75]2[CH:80]=[CH:79][CH:78]=[CH:77][C:76]=2[C:81]([F:82])([F:83])[F:84])[CH2:70][C:71]([OH:73])=[O:72])=[O:28])[CH:5]=1)[CH2:2][CH3:3]

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 5706704HCID 5706704, compoundHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178439324HCID 178439324, compound

Product 1

HCID 178439312HCID 178439312, compoundYield 100%

Procedure

A solution of 5-propyl-1-{6-[2-(1H-tetrazol-5-yl)-phenyl]pyridin-3-ylmethyl}-1H-pyrazole-3-carboxylic acid (20 mg, 0.05 mmol), HATU (19.5 mg, 0.0514 mmol) and DIPEA (44.7 uL, 0.257 mmol) in DMF (1.59 mL, 20.5 mmol) was stirred to pre-activate the acid. After 30 minutes, (R)-3-amino-4-(2-trifluoromethylphenyl)butanoic acid.HCl (14.6 mg, 51.4 μmol)) was added. The resulting solution was stirred overnight. The mixture was concentrated, re-dissolved in water/MeCN/TFA and purified using reverse phase liquid chromatography to yield the title compound (21.1 mg; 100% purity) as a TFA salt. MS m/z: [M+H]+ calcd for C31H29F3N8O3, 619.23; found 619.6.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionre-dissolved in water/MeCN/TFA
  3. custompurified

Sources & evidence

ORD record
ord-3a7444b2ce6341738cfe2b4c0ba0cc20
Source dataset
uspto-grants-2011_06
Patent number
US07956054B2

Reaction notes

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