1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 4-[4-(2-adamantylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate

HRID 1799382Notes

Reaction equation

HRID 1799382 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([S:16][CH2:17][CH2:18][CH3:19])=[C:14]([C:20]([OH:22])=O)[CH:13]=[N:12]2)=[CH:7][CH:6]=1)=[O:4].Cl.[CH:24]12[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH:25]1[NH2:34])[CH2:31]2.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)(=O)C>[CH:24]12[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH:25]1[NH:34][C:20]([C:14]1[CH:13]=[N:12][N:11]([C:8]3[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][CH:9]=3)[C:15]=1[S:16][CH2:17][CH2:18][CH3:19])=[O:22])[CH2:31]2

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 253312-Aminoadamantane hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 595161221-(4-Methoxycarbonylphenyl)-5-propylsulfanyl-pyrazole-4-carboxylic acid2×

Product 1

HCID 53630271Methyl 4-[4-(2-adamantylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(4-methoxycarbonylphenyl)-5-propylsulfanyl-pyrazole-4-carboxylic acid (Intermediate #7) (160 mg, 0.5 mmol), 2-adamantylamine hydrochloride (94 mg, 0.5 mmol), HOBT (81 mg, 0.6 mmol) and DIPEA (261 μL, 1.5 mmol) were dissolved in DMF (5 mL) and treated at ambient temperature with EDCI (115 mg, 0.6 mmol). The mixture was stirred at ambient for 18 h and then diluted with ethyl acetate (50 mL), washed with water (3×20 mL) and brine, dried (MgSO4) and evaporated to leave a white solid, which was purified by chromatography on silica gel, (12 g silica 0-50% EtOAc/isohexane) to give the title compound as a white solid. (203 mg, 92%)

Workup

  1. washwashed with water (3×20 mL) and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customto leave a white solid, which
  5. customwas purified by chromatography on silica gel, (12 g silica 0-50% EtOAc/isohexane)

Sources & evidence

ORD record
ord-380b36326f70491b8e61f746a3411c5f
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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