Triethylamine → HCID 59813972, compound

HRID 2115281Notes

Reaction equation

HRID 2115281 reaction equation
[Cl:1][C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[N:4][N:5]([CH2:8][C:9]([OH:11])=O)[C:6]=1[CH3:7].C(N(CC)CC)C.[C:23]([O:27][C:28]([N:30]1[CH2:37][CH:36]2[CH:32]([CH2:33][NH:34][CH2:35]2)[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>CN(C=O)C>[C:23]([O:27][C:28]([N:30]1[CH2:31][CH:32]2[CH:36]([CH2:35][N:34]([C:9](=[O:11])[CH2:8][N:5]3[C:6]([CH3:7])=[C:2]([Cl:1])[C:3]([C:12]([F:15])([F:14])[F:13])=[N:4]3)[CH2:33]2)[CH2:37]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 1876853(4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acidHCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylate

Product 1

HCID 59813972HCID 59813972, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (4-Chloro-5-methyl-3-trifluoromethylpyrazol-1-yl)acetic acid (97 mg), triethylamine (0.2 mL) and compound 5 (76 mg) in DMF (2 mL) was stirred at 0° C. and 1-propanephosphonic acid cyclic anhydride (0.55 mL, 50% in EtOAc) was added dropwise. The reaction mixture was stirred another 30 min at 0° C. and directly purified by preparative HPLC to provide the title compound 6 as a pale yellow oil (146 mg, 93%). LCMS: Rf: 4.495 min, M+H+: 459.

Workup

  1. customdirectly purified by preparative HPLC

Sources & evidence

ORD record
ord-c3a864f34fb0423ca3547a02df47198e
Source dataset
uspto-grants-2008_10
Patent number
US07435830B2

Reaction notes

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