HCID 82586427, compound → HCID 86700247, compound

HRID 879439Notes

Reaction equation

HRID 879439 reaction equation
[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[C:4]([CH3:11])=[N:3]1.[C:12]([O:16][C@@H:17]([C:23]1[C:38]([CH3:39])=[CH:37][C:26]2[N:27]=[C:28]([C:30]3[CH:35]=[CH:34][N:33]=[C:32](Cl)[CH:31]=3)[S:29][C:25]=2[C:24]=1[C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH3:15])([CH3:14])[CH3:13]>CN1C(=O)CCC1>[C:12]([O:16][C@@H:17]([C:23]1[C:38]([CH3:39])=[CH:37][C:26]2[N:27]=[C:28]([C:30]3[CH:35]=[CH:34][N:33]=[C:32]([N:7]4[CH2:8][CH2:9][C:10]5[N:2]([CH3:1])[N:3]=[C:4]([CH3:11])[C:5]=5[CH2:6]4)[CH:31]=3)[S:29][C:25]=2[C:24]=1[C:40]1[CH:41]=[CH:42][C:43]([Cl:46])=[CH:44][CH:45]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH3:13])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 82586427HCID 82586427, compoundHCID 86700142(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

Product 1

HCID 86700247HCID 86700247, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1,3-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine (47.6 mg, 0.315 mmol), (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (32 mg, 0.060 mmol) in anhydrous NMP (1.0 mL) was heated at 90-110° C. for 40 h. Reaction mixture was cooled to room temperature, filtered through a syringe filter and purified by Gilson HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA). Product-containing fractions were diluted with ethyl acetate, washed with saturated sodium bicarbonate solution. Aqueous layer was back-extracted with ethyl acetate and the combined organic layer was washed with brine, dried (MgSO4), filtered, and concentrated to give product. LCMS-ESI+: calc'd for C35H39ClN5O3S: 644.2 (M+H+); Found: 644.3 (M+H+).

Workup

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. filtrationfiltered through a syringe
  4. filtrationfilter
  5. custompurified by Gilson HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA)
  6. additionProduct-containing fractions were diluted with ethyl acetate
  7. washwashed with saturated sodium bicarbonate solution
  8. extractionAqueous layer was back-extracted with ethyl acetate
  9. washthe combined organic layer was washed with brine
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto give product

Sources & evidence

ORD record
ord-96121b354745491797e90839e4e44eab
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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