Hydrochloric Acid → HCID 11404829, compound

HRID 30498Notes

Reaction equation

HRID 30498 reaction equation
C(S([N:7]=[C:8]([C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:31]=1[N:30]=[CH:29][CH:28]=[CH:27]2)[C:9]1[CH:21]=[CH:20][C:12]([C:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1)=O)(C)(C)C.Cl.CCOCC>CO>[NH2:7][CH:8]([C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:31]=1[N:30]=[CH:29][CH:28]=[CH:27]2)[C:9]1[CH:21]=[CH:20][C:12]([C:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86591914HCID 86591914, compound

Product 1

HCID 11404829HCID 11404829, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Treatment of 15 (135 mg, ˜0.30 mmol) with HCl in ether (0.3 mL, 0.6 mmol) in MeOH (2 mL) at 25° C., for 5 min. Concentration in vacuo, dilution with water, washing with EtOAc. The solution was then made basic with K2CO3(aq), extracted with and evaporated to give (+)-6 (53 mg, 53% from 14). 1H NMR (CDCl3): δ1.2 (m, 6H), 2.2 (s, 2H), 3.4 (m, 4H), 6.40 (s, 1H), 7.30-7.58 (m, 7H), 7.71 (m, 1H), 8.15 (m, 1 H), 8.92 (m, 1H).

Workup

  1. concentrationConcentration in vacuo, dilution with water
  2. washwashing with EtOAc
  3. extractionextracted with and
  4. customevaporated
  5. customto give (+)-6 (53 mg, 53% from 14)

Sources & evidence

ORD record
ord-2db1a262d1224178940b6abdf9d3e3e7
Source dataset
uspto-grants-2008_09
Patent number
US07423154B2

Reaction notes

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