Ammonium Hydroxide → HCID 59174896, compound

HRID 1177419Notes

Reaction equation

HRID 1177419 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[S:12][C:13]2[C:18]([N:19]=1)=[CH:17][CH:16]=[C:15]([C:20]1([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:22][CH2:21]1)[N:14]=2)[C:5](O)=[O:6].[OH-].[NH4+:30]>S(Cl)(Cl)=O.C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[S:12][C:13]2[C:18]([N:19]=1)=[CH:17][CH:16]=[C:15]([C:20]1([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:22][CH2:21]1)[N:14]=2)[C:5]([NH2:30])=[O:6]

Participants

6

Reactant 2

HCID 14923Ammonium HydroxideHCID 573944063-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzoic acid

Product 1

HCID 59174896HCID 59174896, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolvent

Procedure

3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzoic acid (107 mg, 0.274 mmol) was dissolved in thionyl chloride at 65° C. for 1 h before it was concentrated. The reaction mixture was dissolved in THF (1.4 mL) before ammonium hydroxide (1.07 mL, 27.40 mmol) was added and stirred at ambient temp. for 16 h. The reaction mixture was diluted with EtOAc, added to a separatory funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed with sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotovap to give the title compound after preparatory LC. MS (ESI) m/z: Calculated: 389; Observed: 390.1 (M++1).

Workup

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

Sources & evidence

ORD record
ord-49b9f9d037d04826a494baa946693f2d
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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