Hydrochloric Acid → Hydrochloric Acid

HRID 1522046Notes

Reaction equation

HRID 1522046 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH:18]=4)=[CH:16][C:9]=23)[CH:5]=[CH:4][CH:3]=1.[ClH:30].O1CCOCC1>CO>[F:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH:18]=4)=[CH:16][C:9]=23)[CH:5]=[CH:4][CH:3]=1.[ClH:30]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 90412644HCID 90412644, compound

Product 2

HCID 313Hydrochloric AcidHCID 90412052HCID 90412052, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of Example 309E (4.0 g, 10.14 mmol) and 4M HCl in dioxane (25.4 ml, 101 mmol) in methanol (10 mL) was stirred at room temperature for 4 hours. The mixture was concentrated and the solid was washed with ethyl acetate and vacuum dried to provide the title compound as an HCl salt. 1H NMR (400 MHz, DMSO-d6) δ 2.81 (s, 2H), 3.33 (s, 2H), 3.83 (s, 2H), 6.62 (s, 1H), 7.17 (d, J=1.6 Hz, 1H), 7.30 (dd, J=7.9, 2.6 Hz, 1H), 7.68 (d, J=5.2 Hz, 1H), 8.08-8.25 (m, 2H), 8.37 (d, J=5.2 Hz, 1H), 9.46 (s, 2H), 12.44 (s, 1H). MS (ESI+) m/z 295.1 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. washthe solid was washed with ethyl acetate and vacuum
  3. customdried

Sources & evidence

ORD record
ord-e254ca9d7ac1445badf6cd68be54ffcf
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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