Trifluoroacetic acid → HCID 58466264, compound

HRID 335959Notes

Reaction equation

HRID 335959 reaction equation
[F:1][C:2]1([F:40])[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]3[O:13][C:14]4[C:19]([C@@:20]5([CH2:24][S:23][C:22]([NH:25]C(=O)OC(C)(C)C)=[N:21]5)[C:9]=3[CH:8]=2)=[CH:18][C:17]([C:33]2[C:34]([F:39])=[N:35][CH:36]=[CH:37][CH:38]=2)=[CH:16][CH:15]=4)[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:40][C:2]1([F:1])[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]3[O:13][C:14]4[C:19]([C@@:20]5([CH2:24][S:23][C:22]([NH2:25])=[N:21]5)[C:9]=3[CH:8]=2)=[CH:18][C:17]([C:33]2[C:34]([F:39])=[N:35][CH:36]=[CH:37][CH:38]=2)=[CH:16][CH:15]=4)[CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67437844HCID 67437844, compound

Product 1

HCID 58466264HCID 58466264, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 3-(3,3-difluoropyrrolidin-1-yl)-7-(2-fluoropyridin-3-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-thiazole]-2′-ylcarbamate (76.1 mg, 0.13 mmol) in DCM (1.34 mL) was added TFA (280 μL, 3.63 mmol) at ambient temperature. The reaction was stirred at ambient temperature for 68 hours. The reaction was concentrated under reduced pressure and the resulting material was purified by “catch-and release” technique using a Varian Bond ELUT SCX column. The eluate was concentrated under reduced pressure to afford (S)-3-(3,3-difluoropyrolidin-1-yl)-7-(2-fluoropyridin-3-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-thiazol]-2′-amine (52.14 mg, 0.11 mmol, 83% yield).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe resulting material was purified by “
  3. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ce5e357756394d02aef4bc18af0e0e71
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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