Hydrochloric Acid → HCID 17984404, compound

HRID 1181063Notes

Reaction equation

HRID 1181063 reaction equation
C([O:5][C:6](=[O:44])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=4)=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:36][NH:37][C:38]([O:40][CH:41]([CH3:43])[CH3:42])=[O:39])(C)(C)C.Cl>C1COCC1>[CH:41]([O:40][C:38]([NH:37][CH2:36][C:10]1[CH:11]=[C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:25]=[CH:26][C:27]([C:30]4[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=4)=[CH:28][CH:29]=3)[O:21][C:22]=2[CH3:23])[CH:13]=[CH:14][C:9]=1[CH2:8][CH2:7][C:6]([OH:44])=[O:5])=[O:39])([CH3:43])[CH3:42]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69230925HCID 69230925, compound

Product 1

HCID 17984404HCID 17984404, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This ester (225 mg, 0.375 mmol) was dissolved in THF (15 mL) and treated with 1N HCl (1 mL). The mixture was heated at reflux for 7 h, cooled, and concentrated. The residue was azeotroped twice with acetonitrile and dried in a vacuum oven to give the title compound, isolated as the HCl salt (140 mg, 64%). 1H NMR (DMSO-d6) δ1.15 (d, 6H), 2.41 (s, 3H), 2.45 (t, 2H), 2.76 (t, 2H), 2.95 (t, 2H), 4.17 (overlapping t and d, 4H), 4.75 q, 1H), 6.77 (m, 2H), 7.07 (dd, 1H), 7.55 (t, 1H), 8.02 (m, 4H), 8.73 (d, 1H), 8.85 (d, 1H), 9.25 (s, 1H). MS [EI+] m/z 544 (M+H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 7 h
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe residue was azeotroped twice with acetonitrile
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-69329388edb4485a8aae09490dc42eda
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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