Hydrochloric Acid → HCID 59428625, compound

HRID 1515311Notes

Reaction equation

HRID 1515311 reaction equation
C1(C(C2C=CC=CC=2)=[N:8][C:9]2[C:10]3[CH:17]=[CH:16][N:15]([CH2:18][C:19]4[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=4)[C:11]=3[N:12]=[CH:13][CH:14]=2)C=CC=CC=1.Cl>C1COCC1>[N:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:15]2[C:11]3=[N:12][CH:13]=[CH:14][C:9]([NH2:8])=[C:10]3[CH:17]=[CH:16]2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59428634HCID 59428634, compound

Product 1

HCID 59428625HCID 59428625, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 25-mL round-bottomed flask equipped with magnetic stirrer is charged with Compound 1c (0.580 g, 1.49 mmol), THF (10 mL) and 2N hydrochloric acid (2.0 mL). The reaction is then stirred at room temperature for 1 h. After such time, the reaction is partitioned between ethyl acetate (15 mL) and water (15 mL). The aqueous layer is separated and washed with ethyl acetate (2×25 mL). After basifying to pH 9 with solid potassium carbonate in order to liberate the free base of Compound 1d, the aqueous layer is extracted with ethyl acetate (2×25 mL). The extracts are then combined and dried over sodium sulfate. The sodium sulfate is removed by filtration and the filtrate concentrated under reduced pressure. The resulting residue is then purified by column chromatography to afford Compound 1d as a white solid.

Workup

  1. customA 25-mL round-bottomed flask equipped with magnetic stirrer
  2. customAfter such time, the reaction is partitioned between ethyl acetate (15 mL) and water (15 mL)
  3. customThe aqueous layer is separated
  4. washwashed with ethyl acetate (2×25 mL)
  5. extractionthe aqueous layer is extracted with ethyl acetate (2×25 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe sodium sulfate is removed by filtration
  8. concentrationthe filtrate concentrated under reduced pressure
  9. customThe resulting residue is then purified by column chromatography

Sources & evidence

ORD record
ord-9c7cbc6f6063434fb2300257b207ff4b
Source dataset
uspto-grants-2012_07
Patent number
US08222421B2

Reaction notes

Loading…