Trifluoroacetic acid → HCID 89662758, compound

HRID 1479095Notes

Reaction equation

HRID 1479095 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([N:24]2[CH2:38][C:27]3=[C:28]4[N:33]([N:34]=[C:26]3[CH2:25]2)[C:32]([CH3:35])=[C:31]([Cl:36])[C:30]([CH3:37])=[N:29]4)=[O:23])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:36][C:31]1[C:30]([CH3:37])=[N:29][C:28]2[N:33]([N:34]=[C:26]3[CH2:25][N:24]([C:22]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[CH2:15][O:14][C@H:10]4[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]4)=[O:23])[CH2:38][C:27]3=2)[C:32]=1[CH3:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736558HCID 131736558, compound

Product 1

HCID 89662758HCID 89662758, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (S)-3-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-benzyloxy]-piperidine-1-carboxylic acid tert-butyl ester (50 mg; 0.09 mmol; 1 eq.) and TFA (2 mL) in DCM (2 mL) was stirred at room temperature for 30 minutes then concentrated in vacuo. The residue was taken up in water, the pH made basic with 5M NaOH and extracted with DCM (2×). The combined organic layer was dried over magnesium sulfate and concentrated in to afford the title compound (40 mg, 98%) as an off-white solid. 1H NMR (CDCl3) δ 7.39-7.26 (m, 4H), 5.03-4.88 (m, 2H), 4.63-4.47 (m, 4H), 3.63-3.30 (m, 1H), 2.94-2.71 (m, 5H), 2.62-2.53 (m, 3H), 1.83-0.72 (m, 7H). HPLC (max plot) 100%, Rt 2.63 min. UPLC/MS: (MS+) 440.2 ([M+H]+).

Workup

  1. concentrationthen concentrated in vacuo
  2. extractionextracted with DCM (2×)
  3. dry with materialThe combined organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in

Sources & evidence

ORD record
ord-918603a1e9fb4fc395b025817c390c95
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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