Hydrochloric Acid → HCID 131736546, compound

HRID 1479066Notes

Reaction equation

HRID 1479066 reaction equation
Cl.C([O:6][C:7]([N:9]1[CH2:13][CH2:12][C@H:11]([O:14][C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=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])[CH2:10]1)=[O:8])(C)(C)C>O1CCOCC1>[CH:7]([OH:8])=[O:6].[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:16]4[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=4[O:14][C@H:11]4[CH2:12][CH2:13][NH:9][CH2:10]4)=[O:23])[CH2:38][C:27]3=2)[C:32]=1[CH3:35]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 89650323HCID 89650323, compound

Product 1

HCID 131736546HCID 131736546, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

HCl (2.64 mL) was added to a solution of (S)-3-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-5-fluoro-phenoxy]-pyrrolidine-1-carboxylic acid tert-butyl ester (1.4 g; 2.64 mmol; 1 eq.) in 1,4-dioxane (10 mL) and the reaction mixture was stirred at room temperature for 16 hours then concentrated in vacuo. The residue was taken up in DCM, washed with 0.1M NaOH, dried over magnesium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (48 mg, 4%) as a yellow solid. 1H NMR (DMSO-d6) δ 8.28 (s, 1H), 7.44-7.33 (m, 1H), 7.17-7.09 (m, 1H), 6.91 (td, J=8.4, 2.3 Hz, 1H), 5.14-5.06 (m, 1H), 4.86-4.78 (m, 2H), 4.63-4.42 (m, 2H), 3.35-3.21 (m, 1H), 3.08-2.85 (m, 3H), 2.83 (s, 1.5H), 2.80 (s, 1.5H), 2.61 (s, 1.5H), 2.55 (s, 1.5H), 2.16-1.97 (m, 1H), 1.95-1.83 (m, 1H). HPLC (max plot) 93.3%, Rt 2.67 min. UPLC/MS: (MS+) 430.4 ([M+H]+).

Workup

  1. concentrationthen concentrated in vacuo
  2. washwashed with 0.1M NaOH
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by mass

Sources & evidence

ORD record
ord-51c32f22ef4d495ab140d473d316de74
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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