2-Aminoadamantane hydrochloride → Methyl 4-[4-(2-adamantylcarbamoyl)-5-cyclopentylsulfanyl-pyrazol-1-yl]benzoate

HRID 1799423Notes

Reaction equation

HRID 1799423 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH:13]1([S:18][C:19]2[N:23]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:25]=3)[N:22]=[CH:21][C:20]=2[C:34](O)=[O:35])[CH2:17][CH2:16][CH2:15][CH2:14]1.Cl.[CH:38]12[CH2:47][CH:42]3[CH2:43][CH:44]([CH2:46][CH:40]([CH2:41]3)[CH:39]1[NH2:48])[CH2:45]2.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>CN(C=O)C>[CH:38]12[CH2:47][CH:42]3[CH2:43][CH:44]([CH2:46][CH:40]([CH2:41]3)[CH:39]1[NH:48][C:34]([C:20]1[CH:21]=[N:22][N:23]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:25]=3)[C:19]=1[S:18][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1)=[O:35])[CH2:45]2

Participants

7

Reactant 5

HCID 253312-Aminoadamantane hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 595161105-Cyclopentylsulfanyl-1-(4-methoxycarbonylphenyl)pyrazole-4-carboxylic acid2×

Product 1

HCID 59516124Methyl 4-[4-(2-adamantylcarbamoyl)-5-cyclopentylsulfanyl-pyrazol-1-yl]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (199 mg, 1.04 mmol) was added in one portion to 5-(cyclopentylthio)-1-(4-(methoxycarbonyl)phenyl)-1H-pyrazole-4-carboxylic acid (Intermediate #93) (300 mg, 0.87 mmol), 2-Adamantanamine hydrochloride (179 mg, 0.95 mmol), 1-Hydroxybenzotriazole (140 mg, 1.04 mmol) and N-Ethyldiisopropylamine (0.450 mL, 2.60 mmol) in DMF (7 mL) at 20° C. under nitrogen. The resulting mixture was stirred at 20° C. for 18 hours.

Sources & evidence

ORD record
ord-41ee18f2aad74c68bd7bcbf862b767a5
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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