Trifluoroacetic acid → HCID 178511738, compound

HRID 707221Notes

Reaction equation

HRID 707221 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:11][C@H:10]([NH:12][C:13]2[S:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[S:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=[C:13]1[NH:12][C@H:10]1[CH2:9][C@H:8]([NH2:7])[CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454113HCID 178454113, compound2×

Product 1

HCID 178511738HCID 178511738, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl(trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)carbamate (Intermediate 10) (720 mg, 2.262 mmol) was dissolved in dichloromethane (30 mL) and treated with trifluoroacetic acid (2 mL). The solution was stirred at room temperature for 15 minutes then evaporated to dryness under reduced pressure and further dried under high vacuum. 2 N Hydrochloric acid (50 mL) and diethyl ether (100 mL) were added and the phases mixed and separated. The organic was discarded. The aqueous layer was saturated with sodium chloride and the pH adjusted to >10 using 5N sodium hydroxide. Ethyl acetate (200 mL) was added and the phases mixed and separated. The aqueous was extracted with ethyl acetate one more time (200 mL) and the combined organic layers dried with magnesium sulfate before evaporating to dryness under reduced pressure. The crude trans-N-(benzo[d]thiazol-2-yl)cyclobutane-1,3-diamine (459 mg, 2.10 mmol, 92.4% yield) was used without further purification.

Workup

  1. customthen evaporated to dryness under reduced pressure
  2. customfurther dried under high vacuum
  3. addition2 N Hydrochloric acid (50 mL) and diethyl ether (100 mL) were added
  4. additionthe phases mixed
  5. customseparated
  6. additionEthyl acetate (200 mL) was added
  7. additionthe phases mixed
  8. customseparated
  9. extractionThe aqueous was extracted with ethyl acetate one more time (200 mL)
  10. dry with materialthe combined organic layers dried with magnesium sulfate
  11. custombefore evaporating to dryness under reduced pressure

Sources & evidence

ORD record
ord-52a72e93a6a543c48f17899e08a08db6
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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