Hydrochloric Acid → HCID 22462766, compound

HRID 1595923Notes

Reaction equation

HRID 1595923 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[C:15]([CH3:25])[CH:14]=3)=[O:12])=[C:9]([C:26]3[CH:31]=[CH:30][C:29]([NH:32]C(=O)C)=[CH:28][CH:27]=3)[S:8][C:7]=2[CH:36]=1.Cl>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[CH2:21][CH2:22][CH2:23][CH2:24]4)=[C:15]([CH3:25])[CH:14]=3)=[O:12])=[C:9]([C:26]3[CH:27]=[CH:28][C:29]([NH2:32])=[CH:30][CH:31]=3)[S:8][C:7]=2[CH:36]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 22462672HCID 22462672, compound

Product 1

HCID 22462766HCID 22462766, compound

Procedure

A solution of 200 mg (0.40 mmol) of 3-methyl-4-[(1-pyrrolidinyl)methyl]phenyl 6-methoxy-2-(4-acetamidophenyl)benzo[b]thiophen-3-yl ketone (Part H) in 5 mL of MEOH was treated with 5 mL of conc. aq HCl. The reaction was heated to mild reflux for 1 hr and was concentrated in vacuo. The residue was taken up in 25 mL. of H2O, the solution basified to pH 12 with 5 N aq NaOH, and the mixture was extracted with EtOAc (2×25 mL). Trhe comrbined organic extracts were dried (K2CO3), filtered, and concentrated in vacuo to give 175 mg (0.38 mmol; 96%) of the title compound as a foam.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto mild reflux for 1 hr
  3. concentrationwas concentrated in vacuo
  4. extractionthe mixture was extracted with EtOAc (2×25 mL)
  5. dry with materialwere dried (K2CO3)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7c0f6964ac2466b9eddf0b7be0ea52d
Source dataset
uspto-grants-2001_09
Patent number
US06288105B1

Reaction notes

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