HCID 67003839, compound → HCID 67002490, compound

HRID 2362622Notes

Reaction equation

HRID 2362622 reaction equation
[Cl:1][C:2]1[C:3]([C:34]2[S:38][C:37]([C:39]3([O:43]COC)[CH2:42][CH2:41][CH2:40]3)=[N:36][CH:35]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][CH2:17][N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[CH:15]=3)[N:8]([S:24]([C:27]3[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:5]2=[N:6][CH:7]=1>CO.Cl>[Cl:1][C:2]1[C:3]([C:34]2[S:38][C:37]([C:39]3([OH:43])[CH2:40][CH2:41][CH2:42]3)=[N:36][CH:35]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][CH2:17][N:18]4[CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)[CH:15]=3)[N:8]([S:24]([C:27]3[CH:28]=[CH:29][C:30]([CH3:31])=[CH:32][CH:33]=3)(=[O:26])=[O:25])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 67003839HCID 67003839, compound

Product 1

HCID 67002490HCID 67002490, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 4-(2-(4-(5-chloro-4-(2-(1-(methoxymethoxy)cyclobutyl)thiazol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-pyrazol-1-yl)ethyl)morpholine (Example 1G) (80 mg, 0.117 mmol) in methanol (1.95 mL) and 10% aqueous HCl solution (0.39 mL) was heated to 65° C. for 3 hours and was then concentrated to dryness. The residue was partitioned between ethyl acetate and saturated aqueous bicarbonate solution. The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated to give the title compound. MS ESI (−) m/z 639.52 [M−H]−.

Workup

  1. concentrationwas then concentrated to dryness
  2. customThe residue was partitioned between ethyl acetate and saturated aqueous bicarbonate solution
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with additional ethyl acetate (2×)
  5. dry with materialThe combined organics were dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cf6bad0a3cf84d1f8d6f348aad584877
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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