Trifluoroacetic acid → HCID 122436373, compound

HRID 1479094Notes

Reaction equation

HRID 1479094 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][CH2:14][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[CH2:14][O:13][C@H:10]4[CH2:11][CH2:12][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 89650271HCID 89650271, compound

Product 1

HCID 122436373HCID 122436373, compoundYield 104.6%

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]-pyrrolidine-1-carboxylic acid tert-butyl ester (60 mg; 0.11 mmol; 1 eq.) and TFA (2 mL) in DCM (2 mL) was stirred at room temperature for 15 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 (49 mg, quantitative) as an off-white solid. 1H NMR (CDCl3) δ 7.46-7.33 (m, 4H), 5.02-4.95 (m, 2H), 4.68-4.46 (m, 4H), 4.21 (m, 1H), 3.26-2.97 (m, 1H), 2.92-2.82 (m, 3H), 2.70-2.58 (m, 3H), 1.96-1.59 (m, 2H). HPLC (max plot) 100%, Rt 2.56 min. UPLC/MS: (MS+) 426.2 ([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-59296007e73c47918dd854283b3d76c5
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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