Hydrochloric Acid → HCID 86638722, compound

HRID 1177547Notes

Reaction equation

HRID 1177547 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH:9][O:10]C)[CH:5]=[CH:4][C:3]=1[C:12]1[S:13][C:14]2[C:19]([N:20]=1)=[CH:18][CH:17]=[C:16]([C:21]1([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:23][CH2:22]1)[N:15]=2.Cl>O1CCOCC1.C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][CH:9]=[O:10])[CH:5]=[CH:4][C:3]=1[C:12]1[S:13][C:14]2[C:19]([N:20]=1)=[CH:18][CH:17]=[C:16]([C:21]1([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:22][CH2:23]1)[N:15]=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67111633HCID 67111633, compound

Product 1

HCID 86638722HCID 86638722, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

2-(2-Fluoro-4-(2-methoxyvinyl)phenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (570 mg, 1.42 mmol) was dissolved in 1,4-dioxane (14 mL) before concentrated hydrochloric acid (1.18 mL, 14.16 mmol) was added and stirred at 65° C. for 1 h. The reaction mixture was diluted with 100 mL of DCM, added to a separatory funnel, partitioned with 1 N NaOH (aqueous), washed with sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotovap to give 2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)acetaldehyde after flash chromatography. MS (ESI) m/z: Calculated: 388.1; Observed: 389.0 (M++H).

Workup

  1. additionwas added
  2. additionadded to a separatory funnel
  3. custompartitioned with 1 N NaOH (aqueous)
  4. washwashed with sodium bicarbonate (saturated, aqueous)
  5. customseparated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated via rotovap

Sources & evidence

ORD record
ord-0f0ae35bdaeb497e85d5da7d04b0fec1
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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