Dimethylformamide → HCID 178434959, compound

HRID 516459Notes

Reaction equation

HRID 516459 reaction equation
[OH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:5]=[C:4]([C:13]([OH:15])=O)[CH:3]=1.CN(C(ON1N=NC2C=CC(=CC1=2)Cl)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C=O)C.CCN(C(C)C)C(C)C.[CH3:55][C:56]1[O:60][C:59](=[O:61])[O:58][C:57]=1[CH2:62][O:63][C:64](=[O:84])[C@H:65]([OH:83])[CH2:66][C@H:67]([NH2:82])[CH2:68][C:69]1[CH:74]=[CH:73][C:72]([C:75]2[CH:80]=[CH:79][CH:78]=[C:77]([Cl:81])[CH:76]=2)=[CH:71][CH:70]=1>>[CH3:55][C:56]1[O:60][C:59](=[O:61])[O:58][C:57]=1[CH2:62][O:63][C:64](=[O:84])[C@H:65]([OH:83])[CH2:66][C@H:67]([NH:82][C:13]([C:4]1[CH:3]=[C:2]([OH:1])[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:5]=1)=[O:15])[CH2:68][C:69]1[CH:74]=[CH:73][C:72]([C:75]2[CH:80]=[CH:79][CH:78]=[C:77]([Cl:81])[CH:76]=2)=[CH:71][CH:70]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 42624899O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphateHCID 86705143(2R,4R)-4-Amino-5-(3'-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid 5-methyl-2-oxo[1,3]dioxol-4-ylmethyl esterHCID 178524632HCID 178524632, compound

Product 1

HCID 178434959HCID 178434959, compoundYield 80.8%

Procedure

5-Hydroxy-1-pyridin-2-yl-1H-pyrazole-3-carboxylic acid (8.1 mg, 39 μmol) and HCTU (16.2 mg, 39 μmol) were combined in DMF (166 μL, 2.1 mmol) and stirred at room temperature for 15 minutes. DIPEA (19 μL, 0.1 mmol) and (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid 5-methyl-2-oxo[1,3]dioxol-4-ylmethyl ester (15.4 mg, 36 μmol) were added, and the resulting mixture was stirred at room temperature for 30 minutes. The solvent was removed in vacuo and the crude product was purified by preparative HPLC to yield the title compound (18 mg). MS m/z [M+H]+ calc'd for C31H27ClN4O8, 619.15. found 619.1.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. customThe solvent was removed in vacuo
  3. customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-6910f7e16e2b4e1ea8dab65e431e46c8
Source dataset
uspto-grants-2015_08
Patent number
US09108934B2

Reaction notes

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