Hydrochloric Acid → HCID 71610220, compound

HRID 1479064Notes

Reaction equation

HRID 1479064 reaction equation
Cl.C(OC([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)(C)(C)C>O1CCOCC1>[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 122512289HCID 122512289, compound

Product 1

HCID 71610220HCID 71610220, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

HCl (1.3 mL) was added to a solution of (R)-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 (700 mg; 1.32 mmol; 1 eq.) in 1,4-dioxane (10 mL) was stirred at room temperature for 16 hours then concentrated in vacuo. The reaction mixture was diluted with DCM, washed with 0.1M NaOH, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (550 mg, 97%) as yellow foam. 1H NMR (DMSO-d6) δ 7.40-7.31 (m, 1H), 7.09-7.01 (m, 1H), 6.93-6.83 (m, 1H), 5.03-4.93 (m, 1H), 4.86-4.76 (m, 2H), 4.62-4.43 (m, 2H), 3.13-3.02 (m, 1H), 2.84 (s, 1.5H), 2.81 (s, 1.5H), 2.78-2.69 (m, 2H), 2.62 (s, 1.5H), 2.57 (s, 1.5H), 2.07-1.89 (m, 1H), 1.79-1.61 (m, 2H). HPLC (max plot) 97.2%, Rt 2.74 min. UPLC/MS: (MS+) 430.4 ([M+H]+).

Workup

  1. concentrationthen concentrated in vacuo
  2. additionThe reaction mixture was diluted with DCM
  3. washwashed with 0.1M NaOH
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eb949db1bb824b1bac4518b533a6138a
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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