4-Methylmorpholine → HCID 178459163, compound

HRID 535204Notes

Reaction equation

HRID 535204 reaction equation
[NH:1]1[C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]([C:9]([OH:11])=O)=[N:2]1.CCN=C=NCCCN(C)C.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.[NH2:40][C@H:41]([CH2:50][C:51]1[CH:56]=[CH:55][C:54]([C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([F:63])[CH:58]=2)=[CH:53][CH:52]=1)[CH2:42][C@:43]([CH2:48][OH:49])([CH3:47])[C:44]([OH:46])=[O:45]>CN(C=O)C>[C:44]([C@:43]([CH3:47])([CH2:48][OH:49])[CH2:42][C@H:41]([NH:40][C:9]([C:3]1[NH:2][N:1]=[C:5]([C:6]([OH:8])=[O:7])[CH:4]=1)=[O:11])[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([F:63])[CH:58]=2)=[CH:53][CH:52]=1)([OH:46])=[O:45]

Participants

7

Reactant 5

HCID 79724-Methylmorpholine2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 76559Pyrazole-3,5-dicarboxylic acidHCID 68181113(2S,4R)-4-amino-5-(3'-fluorobiphenyl-4-yl)-2-hydroxymethyl-2-methyl-pentanoic acid

Product 1

HCID 178459163HCID 178459163, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3,5-Pyrazoledicarboxylic acid (37.7 mg, 241 μmol, 1.0 eq.), EDCI (42.7 μL, 241 μmol, 1.0 eq.), 4-methylmorpholine (53.1 μL, 2.0 eq.) and 1 HOBt (32.6 mg, 241 μmol, 1.0 eq.) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. A predissolved solution of (2S,4R)-4-amino-5-(3′-fluorobiphenyl-4-yl)-2-hydroxymethyl-2-methyl-pentanoic acid (80 mg, 240 μmol, 1.0 eq.) and 4-methylmorpholine (53.1 μL) in DMF (0.3 mL) was added and the resulting mixture was stirred for 15 minutes. The reaction was quenched by adding AcOH and the product was purified by preparative HPLC and lyophilized to yield the title compound (25 mg). MS m/z [M+H]+ calc'd for C24H24FN3O6, 470.17. found 470.4.

Workup

  1. stirringthe resulting mixture was stirred for 15 minutes
  2. customThe reaction was quenched
  3. additionby adding AcOH
  4. customthe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-ea4e0973d71f4d4c9cd5b9ff557d4a8c
Source dataset
uspto-grants-2014_10
Patent number
US08853427B2

Reaction notes

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