Trifluoroacetic acid → HCID 89662756, compound

HRID 1479086Notes

Reaction equation

HRID 1479086 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([N:23]2[CH2:37][C:26]3=[C:27]4[N:32]([N:33]=[C:25]3[CH2:24]2)[C:31]([CH3:34])=[C:30]([Cl:35])[C:29]([CH3:36])=[N:28]4)=[O:22])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:35][C:30]1[C:29]([CH3:36])=[N:28][C:27]2[N:32]([N:33]=[C:25]3[CH2:24][N:23]([C:21]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[CH:14]=[C:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)=[O:22])[CH2:37][C:26]3=2)[C:31]=1[CH3:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736555HCID 131736555, compound

Product 1

HCID 89662756HCID 89662756, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-benzylidene]-piperidine-1-carboxylic acid tert-butyl ester (80 mg; 0.15 mmol; 1 eq.) and TFA (1 mL) in DCM (1 mL) was stirred at room temperature for 30 min 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 organics were dried over magnesium sulfate and concentrated in vacuo to afford the title compound (40 mg, 62%) as a white solid. 1H NMR (CDCl3) δ 7.41-7.25 (m, 4H), 6.33 (s, 1H), 5.01-5.00 (m, 2H), 4.47-4.45 (m, 2H), 2.90 (s, 2H), 2.85-2.78 (m, 5H), 2.69 (s, 1H), 2.61 (s, 2H), 2.41-2.38 (m, 2H), 2.26-2.23 (m, 2H). HPLC (max plot) 96%, Rt 2.63 min. UPLC/MS: (MS+) 422.2 ([M+H]+).

Workup

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

Sources & evidence

ORD record
ord-2b8b5d2e91024160b298e6f3f429b7c7
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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