Hydrochloric Acid → HCID 68683948, compound

HRID 1713757Notes

Reaction equation

HRID 1713757 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[O:20][C:19]([C:21]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([N:30]3[CH2:35][CH2:34][CH:33]([C:36]([O:38]C(C)(C)C)=[O:37])[CH2:32][CH2:31]3)=[N:28][CH:29]=2)=[O:22])=[N:18][N:17]=1.[ClH:43]>C(Cl)Cl.O1CCOCC1>[ClH:43].[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[O:20][C:19]([C:21]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([N:30]3[CH2:31][CH2:32][CH:33]([C:36]([OH:38])=[O:37])[CH2:34][CH2:35]3)=[N:28][CH:29]=2)=[O:22])=[N:18][N:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acid2×HCID 68683809HCID 68683809, compound

Product 1

HCID 68683948HCID 68683948, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

TFA (0.307 mL; 4.0 mmol) was added to a suspension of tert-Butyl 1-{5-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]pyridin-2-yl}piperidine-4-carboxylate (483 mg; 1.0 mmol) in DCM (5 mL). After 3 days more TFA was added in aliquots (0.31 mL) over 2 days then HCl (1 mL of a 4M solution in 1,4-dioxan) was added. After 24 h the mixture was filtered and the solid was washed with ether and dried under vacuum at 60° C. to give the title compound (193 mg, 42%) as a solid; 1H NMR δ1.55-1.74 (m, 2H), 1.88-2.06 (m, 2H), 2.56-2.69 (m, 1H), 2.69-2.81 (m, 1H), 3.18-3.35 (m, 2H), 4.17 (d, 2H), 7.13-7.22 (m, 1H), 7.24-7.31 (m, 1H), 7.31-7.37 (m, 1H), 7.44 (d, 1H), 7.98-8.09 (m, 1H), 8.19-8.28 (m, 1H), 8.51-8.59 (m, 1H), 10.87 (s, 1H), 11.37 (s, 1H); MS m/e MH+ 427.

Workup

  1. filtrationAfter 24 h the mixture was filtered
  2. washthe solid was washed with ether
  3. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-c6a0b38084c248248dea04315e950a91
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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