Methanol → HCID 67003553, compound

HRID 2362639Notes

Reaction equation

HRID 2362639 reaction equation
[Cl:1][C:2]1[C:3]([C:30]2[S:34][C:33]([C:35]3([O:39]COC)[CH2:38][CH2:37][CH2:36]3)=[N:32][CH:31]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=3)[N:8]([S:20]([C:23]3[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:5]2=[N:6][CH:7]=1.CO>O1CCCC1.Cl>[Cl:1][C:2]1[C:3]([C:30]2[S:34][C:33]([C:35]3([OH:39])[CH2:36][CH2:37][CH2:38]3)=[N:32][CH:31]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=3)[N:8]([S:20]([C:23]3[CH:24]=[CH:25][C:26]([CH3:27])=[CH:28][CH:29]=3)(=[O:22])=[O:21])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 67003670HCID 67003670, compound

Product 1

HCID 67003553HCID 67003553, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-(5-chloro-4-(2-(1-(methoxymethoxy)cyclobutyl)thiazol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)benzoic acid (Example 16A) (700 mg, 1.122 mmol) in tetrahydrofuran (9.3 mL) and 10% aqueous HCl solution (1.9 mL) was heated to 65° C. for 24 hours. An additional 3 mL 10% aqueous HCl solution and 3 mL methanol were added, and the reaction was heated to 80° C. for 3 hours. The reaction was removed from the heat bath and allowed to slowly cool to room temperature. The reaction was diluted with 5 mL water, and the solid was filtered and air-dried to yield the title compound. MS ESI(+) m/z 580.1 [M+H]+;

Workup

  1. customThe reaction was removed from the heat bath
  2. temperatureto slowly cool to room temperature
  3. additionThe reaction was diluted with 5 mL water
  4. filtrationthe solid was filtered
  5. customair-dried

Sources & evidence

ORD record
ord-1f54195949734910983a00e8f59fd10d
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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