Hydrogen chloride-ethyl acetate → 6-Methyl-7-propyl-5,7,13-triazatetracyclo[9.3.1.02,10,04,8]pentadeca-2(10),3,5,8-tetraene hydrochloride

HRID 10090Notes

Reaction equation

HRID 10090 reaction equation
C(OC([N:8]1[CH2:21][CH:20]2[CH2:22][CH:10]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][C:19]=32)[N:16]=[C:15]([CH3:23])[N:14]4[CH2:24][CH2:25][CH3:26])[CH2:9]1)=O)(C)(C)C.C(OCC)(=O)C.[ClH:33]>>[ClH:33].[CH3:23][C:15]1[N:14]([CH2:24][CH2:25][CH3:26])[C:13]2[C:17](=[CH:18][C:19]3[CH:20]4[CH2:22][CH:10]([C:11]=3[CH:12]=2)[CH2:9][NH:8][CH2:21]4)[N:16]=1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 54514832HCID 54514832, compound

Product 1

HCID 867597056-Methyl-7-propyl-5,7,13-triazatetracyclo[9.3.1.02,10,04,8]pentadeca-2(10),3,5,8-tetraene hydrochlorideYield 34%

Conditions

Temperature
100 °C

Procedure

6-Methyl-7-propyl-5,7,13-triazatetracyclo[9.3.1.02,10.04,8]pentadeca-2(10),3,5,8-tetraene-13-carboxylic acid tert-butyl ester (90 mg, 0.253 mmol) was dissolved in 3N HCl ethyl acetate (5 mL) and warmed to 100° C. for ½ hour. The mixture was cooled, concentrated, slurried in ethyl acetate, and filtered to provide a white solid (25 mg, 34%). 1H NMR (400 MHz, DMSO-d6) δ 9.56 (s, NH), 7.91 (s, 1H), 7.83 (br m, NH), 7.74 (s, 1H), 4.38 (m, 2H), 3.48 (m, 2H), 3.32 (m, 2H), 3.10 (m, 2H), 2.87 (s, 3H), 2.28 (m, 1H), 2.15 (d, J=11.0 Hz, 1H) 1.85 (m, 2H), 0.97 (m, 3H). M.p. 147–150° C.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-f83b060476964130952cd72d63482d88
Source dataset
uspto-grants-2006_08
Patent number
US07091372B2

Reaction notes

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