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2-Aminoadamantane hydrochloride → 2'-methyl-2'H-[1,3']bipyrazolyl-4'-carboxylic acid adamantan-2-ylamide

HRID 12829
Notes
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Reaction equation

HRID 12829 reaction equation
[CH3:1][N:2]1[C:6]([N:7]2[CH:11]=[CH:10][CH:9]=[N:8]2)=[C:5]([C:12]([OH:14])=O)[CH:4]=[N:3]1.CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.Cl.[NH2:45][CH:46]1[CH:53]2[CH2:54][CH:49]3[CH2:50][CH:51]([CH2:55][CH:47]1[CH2:48]3)[CH2:52]2>ClCCl.CN(C=O)C.O>[CH:47]12[CH2:55][CH:51]3[CH2:50][CH:49]([CH2:54][CH:53]([CH2:52]3)[CH:46]1[NH:45][C:12]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[N:7]1[CH:11]=[CH:10][CH:9]=[N:8]1)=[O:14])[CH2:48]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 253312-Aminoadamantane hydrochlorideHCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 589728492'-methyl-2'H-[1,3']bipyrazolyl-4'-carboxylic acid2×

Product 1

HCID 250135412'-methyl-2'H-[1,3']bipyrazolyl-4'-carboxylic acid adamantan-2-ylamide
Yield 77%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2′-Methyl-2′H-[1,3′]bipyrazolyl-4′-carboxylic acid (Intermediate 8, 50 mg, 0.26 mmol) was dissolved in a mixture of dry dichloromethane (3.2 mL) and dry DMF (0.8 mL). DIPEA (0.23 mL, 1.3 mmol) and TSTU (93 mg, 0.28 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 (58 mg, 0.31 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 prep-HPLC with a gradient of 10-100% acetonitrile/water to give 2′-methyl-2′H-[1,3′]bipyrazolyl-4′-carboxylic acid adamantan-2-ylamide (65 mg, 77%). Mass spectrum: m/z: 362.2 (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-e39314f40e6043cb9d02def678859e3f
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