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Water → Methyl 3-nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzoate

HRID 1177517
Notes
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Reaction equation

HRID 1177517 reaction equation
[NH2:1][C:2]1[C:3](=[S:17])[NH:4][C:5]([C:8]2([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.Cl[C:19]([C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[N+:31]([O-:33])=[O:32])=O.O.CC1(C)[C@@H]2CC[C@@]1(CS(O)(=O)=O)C(=O)C2>C1(C)C=CC=CC=1.CCOC(C)=O>[N+:31]([C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][C:21]=1[C:19]1[S:17][C:3]2[C:2]([N:1]=1)=[CH:7][CH:6]=[C:5]([C:8]1([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:10][CH2:9]1)[N:4]=2)[C:25]([O:27][CH3:28])=[O:26])([O-:33])=[O:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 65617D-Camphorsulfonic AcidHCID 198054504-Chlorocarbonyl-3-nitrobenzoic acid methyl esterHCID 591748363-amino-6-(1-phenylcyclopropyl)pyridine-2(1H)-thione

Product 1

HCID 67112770Methyl 3-nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzoate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A slurry of 3-amino-6-(1-phenylcyclopropyl)pyridine-2(1H)-thione (1.00 g, 4.13 mmol) and methyl 4-(chlorocarbonyl)-3-nitrobenzoate (1.11 g, 4.54 mmol) in 10 mL toluene was heated under nitrogen with a water cooled reflux condenser was heated in a 120° C. oil bath. After bubbling had subsided, ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonic acid (0.479 g, 2.06 mmol) was added through the condenser and heating continued for 30 min. The slurry was treated with 5 mL toluene to and heating continued overnight to give a dark brown solution. The reaction mixture was cooled to ambient temperature, then diluted with EtOAc, washed with water, sat'd aq. Bicarbonate, and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give a brown oil. Purification by silica gel chromatography, 40 g, 0-30% EA/hexanes gave methyl 3-nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzoate as a light brown solid. MS (ESI) m/z: Calculated: 431.1; Observed: 432.0 (M++1).

Workup

  1. temperaturecooled
  2. temperaturereflux condenser
  3. customAfter bubbling
  4. temperatureheating
  5. temperatureheating
  6. waitcontinued overnight
  7. customto give a dark brown solution
  8. temperatureThe reaction mixture was cooled to ambient temperature
  9. washwashed with water
  10. dry with materialThe organic layer was dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customto give a brown oil
  14. customPurification by silica gel chromatography, 40 g, 0-30% EA/hexanes

Sources & evidence

ORD record
ord-36c70ff257904759b5a52680269d6fdf
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842685B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes