Hydrochloric Acid → HCID 118104179, compound

HRID 522780Notes

Reaction equation

HRID 522780 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[C:9]2[C:5]([C:6]([S:28][C:29]3[C:30]([F:40])=[C:31]([CH:37]=[CH:38][CH:39]=3)[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:7]([CH:25]3[CH2:27][CH2:26]3)[N:8]2[C:12]2[CH:13]=[N:14][N:15](COCC[Si](C)(C)C)[CH:16]=2)=[CH:4][CH:3]=1.Cl.CCN(CC)CC.CCCCC>CCO>[Cl:1][C:2]1[C:10]([F:11])=[C:9]2[C:5]([C:6]([S:28][C:29]3[C:30]([F:40])=[C:31]([CH:37]=[CH:38][CH:39]=3)[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:7]([CH:25]3[CH2:26][CH2:27]3)[N:8]2[C:12]2[CH:13]=[N:14][NH:15][CH:16]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8003PentaneHCID 8471TriethylamineHCID 131735541HCID 131735541, compound

Product 1

HCID 118104179HCID 118104179, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of compound 3 (140 mg, 0.23 mmol) in EtOH (17 mL) was added 3 N HCl (4 mL) at RT and heated to reflux for 3 h. After completion of the reaction (TLC), the pH of the mixture was neutralized with Et3N (2 mL) and extracted with EtOAc (2×30 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the crude. The crude was titurated with n-pentane, dried under reduced pressure to afford 4 (90 mg, 90%) as a pale brown solid. 1H NMR (500 MHz, DMSO-d6): 13.21 (br s, 1H), 8.24 (s, 1H), 7.84 (s, 1H), 7.60 (t, J=6.5 Hz, 1H), 7.21-7.11 (m, 3H), 6.84 (t, J=6.5 Hz, 1H), 4.34 (q, 2H), 1.81-1.76 (m, 1H), 1.32 (t, J=8.0 Hz, 3H), 0.93-0.90 (m, 2H), 0.84-0.79 (m, 2H); LC-MS (ESI): m/z 474.9 (M+H+).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. customAfter completion of the reaction (TLC)
  4. extractionextracted with EtOAc (2×30 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto obtain the crude
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-6b7677f7ce3f4d75866e60d42efe2e3c
Source dataset
uspto-grants-2016_05
Patent number
US09334261B2

Reaction notes

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