Dichloromethane → HCID 178439315, compound

HRID 71654Notes

Reaction equation

HRID 71654 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=CC(C3C=CC=CC=3C3NN=NN=3)=[CH:12][CH:11]=2)[N:7]=[C:6]([C:27]([OH:29])=O)[CH:5]=1)[CH2:2][CH3:3].[CH:30]1[CH:35]=[N:34][C:33]2[N:36](O)[N:37]=[N:38][C:32]=2[CH:31]=1.CCN=C=NCCCN(C)C.N1C(C)=C[CH:54]=[CH:53][C:52]=1[CH3:58].C(Cl)Cl.Cl.[NH2:63][C@H:64]([CH2:69][C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)[CH2:65][C:66]([OH:68])=[O:67]>>[C:70]1([CH2:69][C@@H:64]([NH:63][C:27]([C:6]2[CH:5]=[C:4]([CH2:1][CH2:2][CH3:3])[N:8]([CH2:9][C:10]3[CH:11]=[CH:12][C:30]([C:31]4[CH:54]=[CH:53][CH:52]=[CH:58][C:32]=4[C:33]4[NH:36][N:37]=[N:38][N:34]=4)=[CH:35][CH:15]=3)[N:7]=2)=[O:29])[CH2:65][C:66]([OH:68])=[O:67])[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1

Participants

7

Reactant 6

HCID 6344DichloromethaneHCID 79372,6-LutidineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 24820568(3R)-3-Amino-4-phenylbutanoic acid--hydrogen chloride (1/1)HCID 178439323HCID 178439323, compound

Product 1

HCID 178439315HCID 178439315, compoundYield 92%

Conditions

Temperature
0 °C

Procedure

A solution of 5-propyl-1-[2′-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-1H-pyrazole-3-carboxylic acid (200 mg, 510 μmol), HOAt (77.1 mg, 566.4 μmol), EDCI (108.6 mg, 566.4 μmol), and 2,6-lutidine (357.8 μL, 3.1 mmol) in DCM (6.1 mL, 94.7 mmol) was stirred to pre-activate the acid. After 30 minutes, the mixture was cooled at 0° C. and (R)-3-amino-4-phenylbutyric acid hydrochloride (122.2 mg, 566.4 μmol) was added. The resulting solution was slowly warmed to room temperature and stirred overnight. The mixture was then concentrated, re-dissolved in water/MeCN/TFA and purified using reverse phase liquid chromatography to yield the title compound (59 mg; 92% purity). MS m/z: [M+H]+ calcd for C31H31N7O3, 550.25. found 550.4.

Workup

  1. temperatureThe resulting solution was slowly warmed to room temperature
  2. concentrationThe mixture was then concentrated
  3. dissolutionre-dissolved in water/MeCN/TFA
  4. custompurified

Sources & evidence

ORD record
ord-909fe3b72454462792c62dcdbaae4ad1
Source dataset
uspto-grants-2014_09
Patent number
US08822522B2

Reaction notes

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