1-Hydroxybenzotriazole → HCID 178523477, compound

HRID 1093825Notes

Reaction equation

HRID 1093825 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[NH:20][N:19]=[C:18]([C:21]([NH:23][CH2:24][C:25]([OH:27])=O)=[O:22])[CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.Cl.[CH:52]12[CH2:61][CH:56]3[CH2:57][CH:58]([CH2:60][CH:54]([CH2:55]3)[CH:53]1[NH:62][CH:63]1[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1)[CH2:59]2>CN(C=O)C.O>[CH:54]12[CH2:55][CH:56]3[CH2:57][CH:58]([CH2:59][CH:52]([CH2:61]3)[CH:53]1[NH:62][CH:63]1[CH2:68][CH2:67][N:66]([C:25](=[O:27])[CH2:24][NH:23][C:21]([C:18]3[CH:17]=[C:16]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=4)[NH:20][N:19]=3)=[O:22])[CH2:65][CH2:64]1)[CH2:60]2

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66591568HCID 66591568, compoundHCID 178525878HCID 178525878, compound

Product 1

HCID 178523477HCID 178523477, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (150 mg, 3.5 mmol) was added to a stirred solution [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (150 mg, 0.53 mmol) in DMF (4 mL) followed by HOBt (82 mg, 0.61 mmol) and EDCI.HCl (270 mg, 1.4 mmol). After 2 minutes of stirring, adamantan-2-yl-piperidin-4-yl-amine dihydrochloride (150 mg, 0.59 mmol) was added and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with water and the precipitate was filtered to afford 200 mg (81.63% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(adamantan-2-ylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 462.28, 91.77%. 1H NMR (300 MHz, DMSO-d6): δ8.2-8.0 (bs, 1H), 7.82-7.76 (d, 2H), 7.5-7.42 (t, 2H), 7.4-7.34 (t, 1H), 7.2-7.1 (bs, 1H), 4.3-4.1 (m, 3H), 3.8 (d, 1H), 3.1 (t, 1H), 2.9-2.7 (m, 3H), 2.1 (d, 2H), 1.9-1.6 (m, 1H), 1.4-1.3 (d, 3H), 1.2-1.1 (m, 2H).

Workup

  1. stirringstirring
  2. waitwas continued at ambient temperature overnight
  3. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-cd0051142ba04f9f9cfd65e5fc8b0cbe
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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