Trifluoroacetic acid → HCID 71610248, compound

HRID 1479074Notes

Reaction equation

HRID 1479074 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([O: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])[CH2:9]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[O:14][C@H:10]4[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]4)=[O:22])[CH2:37][C:26]3=2)[C:31]=1[CH3:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89649742HCID 89649742, compound

Product 1

HCID 71610248HCID 71610248, compoundYield 81%

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)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (270 mg; 0.51 mmol; 1 eq.) and TFA (2 mL) in DCM (2 mL) was stirred at room temperature for 1 hour 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 vacuo to afford the title compound (176 mg, 81%) as white foam. 1H NMR (CDCl3) δ 7.41-7.33 (m, 2H), 7.08-6.98 (m, 2H), 5.02-5.01 (m, 2H), 4.67 (br s, 2H), 4.33 (br s, 1H), 3.11-3.06 (m, 1H), 2.91 (s, 2H), 2.85 (s, 1H), 2.84-2.72 (m, 3H), 2.69 (s, 1H), 2.62 (s, 2H), 1.98-1.91 (m, 1H), 1.80-1.69 (m, 3H), 1.50-1.40 (m, 1H). HPLC (max plot) 98.9%, Rt 2.85 min. UPLC/MS: (MS+) 426.4 ([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 vacuo

Sources & evidence

ORD record
ord-2257e7c21b1f422a8c0834595cc5a42a
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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