1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1'-{[3,5-Diethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl]carbonyl}-6-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)spiro[chroman-2,4'-piperidin]-4-one

HRID 1096895Notes

Reaction equation

HRID 1096895 reaction equation
Cl.[O:2]=[C:3]1[NH:7][N:6]=[C:5]([C:8]2[CH:9]=[C:10]3[C:20](=[CH:21][CH:22]=2)[O:19][C:13]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:12][C:11]3=[O:23])[NH:4]1.[CH2:24]([O:26][C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([O:42][CH2:43][CH3:44])[C:35]=1[C:36]1[CH:37]=[N:38][N:39]([CH3:41])[CH:40]=1)[C:30](O)=[O:31])[CH3:25].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O.C(N(CC)CC)C>[CH2:24]([O:26][C:27]1[CH:28]=[C:29]([C:30]([N:16]2[CH2:17][CH2:18][C:13]3([CH2:12][C:11](=[O:23])[C:10]4[C:20](=[CH:21][CH:22]=[C:8]([C:5]5[NH:4][C:3](=[O:2])[NH:7][N:6]=5)[CH:9]=4)[O:19]3)[CH2:14][CH2:15]2)=[O:31])[CH:33]=[C:34]([O:42][CH2:43][CH3:44])[C:35]=1[C:36]1[CH:37]=[N:38][N:39]([CH3:41])[CH:40]=1)[CH3:25]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 579310273,5-diethoxy-4-(1-methyl-1H-pyrazol-4-yl)benzoic acidHCID 1363426456-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)spiro[chroman-2,4'-piperidin]-4-one hydrochloride

Product 1

HCID 1359101741'-{[3,5-Diethoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl]carbonyl}-6-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)spiro[chroman-2,4'-piperidin]-4-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

6-(5-Oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (202 mg), 3,5-diethoxy-4-(1-methyl-1H-pyrazol-4-yl)benzoic acid (145 mg), EDCI (115 mg), HOBT (91.2 mg) and triethylamine (0.209 mL) were suspended in DMF (3 mL), and stirred at 50° C. for 16 hours. Water was added to it, the formed solid was taken out through filtration, and the resulting solid was recrystallized from methanol to obtain the title compound. 1H-NMR (400 MHz, DMSO-d6) δ: 8.08-8.04 (2.0H, m), 8.00 (1.0H, dd, J=8.8, 2.2 Hz), 7.93-7.91 (1.0H, m), 7.25 (1.0H, d, J=8.5 Hz), 7.22 (2.0H, br s), 6.68 (2.0H, s), 4.37-4.13 (1.0H, m), 4.08 (4.0H, q, J=6.8 Hz), 3.86 (3.0H, s), 3.66-3.13 (3.0H, m), 2.95 (2.0H, s), 2.14-1.69 (4.0H, m), 1.37 (6.0H, t, J=7.0 Hz). MS [M+H]+=573.

Workup

  1. filtrationthe formed solid was taken out through filtration
  2. customthe resulting solid was recrystallized from methanol

Sources & evidence

ORD record
ord-0d4e3ac964af4e129a3f466b7d54b9cb
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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