Hydrochloric Acid → HCID 19603730, compound

HRID 1604682Notes

Reaction equation

HRID 1604682 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([C:29]([O:31]C)=[O:30])=[CH:26][CH:27]=5)[C:22]([C:33]#[N:34])=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O.Cl>CO>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([C:29]([OH:31])=[O:30])=[CH:26][CH:27]=5)[C:22]([C:33]#[N:34])=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 19603670HCID 19603670, compound

Product 1

HCID 19603730HCID 19603730, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-3-cyanoindole-5-carboxylate (1.09 g) and sodium hydroxide (1.5 g) in a mixed solvent of water (15 ml) and methanol (30 ml) was stirred under reflux for 2 hours. After cooling, the mixture was made acidic with diluted hydrochloric acid, and the resulting precipitates were collected by filtration and washed with water to give 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-3-cyanoindole-5-carboxylic acid. Borane-methyl sulfide complex (2.0M) in tetrahydrofuran (1.4 ml) was added to a mixture of the acid obtained above in tetrahydrofuran (25 ml) and the mixture was stirred at room temperature for 1 day. After addition of methanol to mixture, the resulting mixture was evaporated under reduced pressure. The residue was partitioned between diluted hydrochloric acid and ethyl acetate. The ethyl acetate layer was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of toluene and ethyl acetate. The fractions containing the objective compounds were combined and concentrated under reduced pressure to give 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-(hydroxymethyl)indole-3-carbonitrile (0.87 g).

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureAfter cooling
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-1f0cb39bf2f94f1796e3b27f004831e5
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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