Diisopropylethylamine → HCID 59490443, compound

HRID 2383490Notes

Reaction equation

HRID 2383490 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][NH:17][CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.Cl.[N:33]1([C:38](=N)[NH2:39])C=CC=N1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][N:17]([C:38]([NH2:39])=[NH:33])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 594904033-(4-methoxybenzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine

Product 1

HCID 59490443HCID 59490443, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-methoxy-benzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine (0.193 g, 0.65 mmol) in dichloromethane (10 mL) and Hunig's Base (0.34 mL, 1.95 mmol) was added 1H-pyrazole-1-carboximidamide hydrochloride (0.100 g, 0.69 mmol). The reaction mixture was stirred at room temperature for 2 hours. A white precipitates was formed, which was filtered, washed with dichloromethane and hexane to give the desired product, 3-(4-methoxy-benzyl)-3,6,8,9-tetrahydro-pyrazolo[3,4-c][2,7]naphthyridine-7-carboxamidine as a white solid (0.088 g, 40%). M.p.=255-256° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.35 (s, 1H), 8.26 (s, 1H), 7.63 (s, 4H), 7.22-7.16 (m, 2H), 6.88-6.82 (m, 2H), 5.60 (s, 2H), 4.75 (s, 2H), 3.76 (t, J=6.4 Hz, 2H), 3.69 (s, 3H), 3.21 (t, J=6 Hz, 2H); LCMS [M+H]: 337.

Workup

  1. customA white precipitates
  2. customwas formed
  3. filtrationwhich was filtered
  4. washwashed with dichloromethane and hexane

Sources & evidence

ORD record
ord-cb7a3bb28ed7450386f72025cc11f977
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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