Hydrochloric Acid → HCID 58730946, compound

HRID 1994206Notes

Reaction equation

HRID 1994206 reaction equation
C([Si](C)(C)[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH:14]=[C:9]2[CH:8]=[CH:7]1)(C)(C)C.Cl.C([O-])(O)=O.[Na+].C(OCC)(=O)C>CO>[N:27]1[CH:26]=[CH:25][CH:24]=[N:23][C:22]=1[O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:13]1[CH:14]=[C:9]2[CH:8]=[CH:7][NH:6][C:10]2=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 58730930HCID 58730930, compoundHCID 86584982Sodium bicarbonate ethyl acetate

Product 1

HCID 58730946HCID 58730946, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 40 prepared above (120 mg, approx. 0.24 mmol), MeOH (1.1 mL) and 10% aq. HCl (2.4 mL) were stirred at room temperature for 1 h then poured onto saturated aq. NaHCO3/ethyl acetate. The aqueous phase was extracted with more ethyl acetate and the combined organic extracts dried (MgSO4) and concentrated to give pure product 41 (40.8 mg, 44% over 3 steps from 26); 1H NMR (400 MHz, CDCl3) δ 6.40 (dd, J=3.4, 1.6 Hz, 1H), 6.76 (t, J=4.8 Hz, 1H), 7.21 (m, 2H), 7.32 (dt, J=7.8 Hz, 1.8 Hz, 1H), 7.39 (dt, J=7.8, 1.8 Hz, 1H), 7.46 (dd, J=7.5, 1.8 Hz, 1H), 8.04 (d, J=2.0 Hz, 1H), 8.30 (d, J=4.8 Hz, 2H), 8.37 (d, J=2.0 Hz, 1H), 10.26 (bs, NH).

Workup

  1. extractionThe aqueous phase was extracted with more ethyl acetate
  2. dry with materialthe combined organic extracts dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-66f5a562788740cd9e9d31007f5c36b6
Source dataset
uspto-grants-2010_01
Patent number
US07652137B2

Reaction notes

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