Trifluoroacetic acid → HCID 21912779, compound

HRID 1245589Notes

Reaction equation

HRID 1245589 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:23][C:24]([F:27])([F:26])[F:25])[N:16]=[C:17]3[C:22]=2[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:27][C:24]([F:25])([F:26])[CH2:23][N:15]1[C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[C:22]2[C:17]([CH2:18][CH2:19][CH2:20][CH2:21]2)=[N:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21912773HCID 21912773, compound

Product 1

HCID 21912779HCID 21912779, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 500 mg (1.3 mmol) of 1-tert-butoxycarbonyl-4-(2-(2,2,2-trifluoroethyl)-4,5,6,7-tetrahydro-(2H)-indazol-3-yl)piperidine (from Step B) in 4.1 mL of CH2Cl2 at 0° C. was treated with 2.7 mL of trifluoroacetic acid. After 30 min volatiles were removed under reduced pressure. The residue was partitioned between 25 mL of CH2Cl2 and 25 mL of 1 N NaOH. After separating phases, the aqueous layer was extracted with 25 mL of 1 N NaOH. The combined organic layers were dried over Na2SO4 and concentrated to afford the title compound, which was used without further purification. 1H-NMR (500 MHz) δ 1.68–1.95 (m, 9H), 2.61–2.71 (m, 7H), 3.17–3.20 (m, 2H), 4.61 (q, J=8.3, 2H).

Workup

  1. customAfter 30 min volatiles were removed under reduced pressure
  2. customThe residue was partitioned between 25 mL of CH2Cl2 and 25 mL of 1 N NaOH
  3. customAfter separating phases
  4. extractionthe aqueous layer was extracted with 25 mL of 1 N NaOH
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-864fbf11c5dd46028420fbb8b3cf856e
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Reaction notes

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