HCID 89649744, compound → HCID 131736554, compound

HRID 1479084Notes

Reaction equation

HRID 1479084 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([N:22]2[CH2:36][C:25]3=[C:26]4[N:31]([N:32]=[C:24]3[CH2:23]2)[C:30]([CH3:33])=[C:29]([Cl:34])[C:28]([CH3:35])=[N:27]4)=[O:21])[CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[ClH:34].[NH:8]1[CH2:9][CH:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([N:22]2[CH2:36][C:25]3=[C:26]4[N:31]([N:32]=[C:24]3[CH2:23]2)[C:30]([CH3:33])=[C:29]([Cl:34])[C:28]([CH3:35])=[N:27]4)=[O:21])[CH2:11]1

Participants

4

Reactant 1

HCID 89649744HCID 89649744, compound

Product 1

HCID 131736554HCID 131736554, compoundYield 2.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-phenoxymethyl]-azetidine-1-carboxylic acid tert-butyl ester (920 mg; 1.8 mmol; 1 eq.) in TFA (5 mL) and DCM (5 mL) was stirred at room temperature for 1 hour and 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. Purification by mass directed preparative HPLC afforded the title compound (10 mg, 1%) a yellow gum. 1H NMR (CDCl3) δ 10.56 (s, 1H), 8.82 (s, 1H), 7.50-7.40 (m, 2H), 7.15-7.02 (m, 2H), 5.09 (s, 0.6H), 5.05 (s, 1.4H), 4.83 (s, 1.4H), 4.70 (s, 0.6H), 4.43-4.27 (m, 3H), 3.93-3.78 (m, 1H), 3.21-3.09 (m, 1H), 3.03 (s, 2H), 2.92 (s, 1H), 2.79 (s, 2H), 2.78 (s, 1H). HPLC (max plot) 99.3%, Rt 2.65 min. UPLC/MS: (MS+) 412.4 ([M+H]+).

Workup

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

Sources & evidence

ORD record
ord-6470131a84db4ccfa865e9567e814493
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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