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2-Aminoadamantane hydrochloride → 5-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide

HRID 12831
Notes
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Reaction equation

HRID 12831 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]([OH:10])=O.CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.Cl.[NH2:41][CH:42]1[CH:49]2[CH2:50][CH:45]3[CH2:46][CH:47]([CH2:51][CH:43]1[CH2:44]3)[CH2:48]2>ClCCl.CN(C=O)C.O>[CH:43]12[CH2:51][CH:47]3[CH2:46][CH:45]([CH2:50][CH:49]([CH2:48]3)[CH:42]1[NH:41][C:8]([C:3]1[CH:4]=[N:5][N:6]([CH3:7])[C:2]=1[Cl:1])=[O:10])[CH2:44]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 253312-Aminoadamantane hydrochlorideHCID 81531DiisopropylethylamineHCID 27357745-Chloro-1-methyl-1H-pyrazole-4-carboxylic acidHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate

Product 1

HCID 250135435-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamideYield 60%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

5-Chloro-1-methyl-1H-pyrazole-4-carboxylic acid (64 mg, 0.4 mmol, CAS#: 54367-66-7, purchased from Oakwood) was dissolved in a mixture of dry dichloromethane (3.2 mL) and dry DMF (0.8 mL). DIPEA (0.28 mL, 1.6 mmol) and TSTU (145 mg, 0.44 mmol) were added to the above mixture. After the mixture was stirred for 1 h, the appearance of active ester was detected by LC-MS. Then 2-aminoadamantane hydrochloride (75 mg, 0.4 mmol) was added. After another 2 hours water was added and the organic layer was separated. The aqueous layer was extracted twice with dichloromethane. The combined organic phases were dried under vacuum and purified by C-18 reversed phase HPLC with a gradient of 10-100% acetonitrile/water to give 5-chloro-1-methyl-1H-pyrazole-4-carboxylic acid adamantan-2-ylamide (70 mg, 60%). Mass spectrum: m/z: 294.1 (M+1).

Workup

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

Sources & evidence

ORD record
ord-00ba1c16f1b0406f8ac1ff0d65001f8a
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