Pyrazole-3,5-dicarboxylic acid → HCID 178472572, compound

HRID 2273477Notes

Reaction equation

HRID 2273477 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C@H:5]([OH:22])[CH2:6][CH:7]([NH2:21])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH3:2].[NH:24]1[C:28]([C:29]([OH:31])=O)=[CH:27][C:26]([C:32]([OH:34])=O)=[N:25]1.[CH3:35][O:36][CH2:37][CH2:38][NH:39][CH3:40].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>[CH2:1]([O:3][C:4](=[O:23])[C@H:5]([OH:22])[CH2:6][CH:7]([NH:21][C:29]([C:28]1[NH:24][N:25]=[C:26]([C:32](=[O:34])[N:39]([CH2:38][CH2:37][O:36][CH3:35])[CH3:40])[CH:27]=1)=[O:31])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:13][CH:14]=1)[CH3:2]

Participants

7

Reactant 5

HCID 76559Pyrazole-3,5-dicarboxylic acidHCID 81531DiisopropylethylamineHCID 300977(2-Methoxyethyl)(methyl)amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67969323HCID 67969323, compound

Product 1

HCID 178472572HCID 178472572, compoundYield 1.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-4-Amino-5-biphenyl-4-yl-2-hydroxypentanoic acid ethyl ester (900 mg, 3.0 mmol, 1.0 eq.), 3,5-pyrazoledicarboxylic acid (448 mg, 2.9 mmol, 1.0 eq.), N-(2-methoxyethyl)methylamine (256 mg, 2.9 mmol, 1.0 eq.), and HATU (1090 mg, 2.9 mmol, 1.0 eq.) were combined in DMF (5 mL), and the resulting mixture was stirred for 2 minutes. DIPEA (1 mL) was added and the mixture was stirred for 1 hour. The mixture was dried under vacuum, and the product was purified using reverse phase chromatography (10-70% MeCN/H2O; 0.05% TFA over 70 minutes) to yield (R)-5-biphenyl-4-yl-2-hydroxy-4-({5-[(2-methoxyethyl)methylcarbamoyl]-2H-pyrazole-3-carbonyl}amino)-pentanoic acid ethyl ester (25 mg) as a TFA salt.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. customThe mixture was dried under vacuum
  3. customthe product was purified
  4. customphase chromatography (10-70% MeCN/H2O; 0.05% TFA over 70 minutes)

Sources & evidence

ORD record
ord-acd9737b696e4a6daf709a4654beca72
Source dataset
uspto-grants-2015_09
Patent number
US09120747B2

Reaction notes

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