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Diisopropylethylamine → 1-cyclopropyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide

HRID 12836
Notes
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Reaction equation

HRID 12836 reaction equation
[CH:1]1([N:4]2[C:8]([C:9]([F:12])([F:11])[F:10])=[C:7]([C:13]([OH:15])=O)[CH:6]=[N:5]2)[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.[NH2:45][CH:46]1[CH:53]2[CH2:54][C:49]3([OH:56])[CH2:50][CH:51]([CH2:55][CH:47]1[CH2:48]3)[CH2:52]2>ClCCl.CN(C=O)C.O>[OH:56][C:49]12[CH2:54][CH:53]3[CH2:52][CH:51]([CH2:55][CH:47]([CH:46]3[NH:45][C:13]([C:7]3[CH:6]=[N:5][N:4]([CH:1]4[CH2:2][CH2:3]4)[C:8]=3[C:9]([F:10])([F:11])[F:12])=[O:15])[CH2:48]1)[CH2:50]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 28574474-Aminoadamantan-1-olHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 589728211-cyclopropyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid2×

Product 1

HCID 250138571-cyclopropyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1-Cyclopropyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (Intermediate 6, 100 mg, 0.45 mmol) was dissolved in a mixture of dry dichloromethane (4 mL) and dry DMF (1 mL). DIPEA (0.5 mL, 2.9 mmol) and TSTU (165 mg, 0.5 mmol) were added to the above mixture. After the mixture was stirred for 2 h, the appearance of active ester was detected by LC-MS. Then 4-amino-adamantan-1-ol (77 mg, 0.46 mmol) was added. After another 4 hours water was added and the organic layer was separated. The aqueous layer was extracted twice with dichloromethane. The combined organic layers were dried under vacuum. The crude mixture was purified by C-18 reversed phase preparative-HPLC with a gradient of 10-100% acetonitrile/water to give 1-cyclopropyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide (79 mg, 48%. Mass spectrum: m/z: 370.2 (M+1).

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted twice with dichloromethane
  3. customThe combined organic layers were dried under vacuum
  4. customThe crude mixture was purified by C-18

Sources & evidence

ORD record
ord-1d5669c1dacf4500b4f798b19027bbba
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728029B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes