Hydrochloric Acid → HCID 122429360, compound

HRID 1479075Notes

Reaction equation

HRID 1479075 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([N:24]2[CH2:38][C:27]3=[C:28]4[N:33]([N:34]=[C:26]3[C:25]2([CH3:40])[CH3:39])[C:32]([CH3:35])=[C:31]([Cl:36])[C:30]([CH3:37])=[N:29]4)=[O:23])[CH2:11][CH2:10]1)=O)(C)(C)C.O>O1CCOCC1>[ClH:36].[Cl:36][C:31]1[C:30]([CH3:37])=[N:29][C:28]2[N:33]([N:34]=[C:26]3[C:25]([CH3:39])([CH3:40])[N:24]([C:22]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[O:15][CH:12]4[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]4)=[O:23])[CH2:38][C:27]3=2)[C:32]=1[CH3:35]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 122512294HCID 122512294, compound

Product 1

HCID 122429360HCID 122429360, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

A 4M solution of HCl in 1,4-dioxane (0.55 mL; 2.21 mmol; 4 eq.) was added to a suspension of 4-[2-(6-chloro-1,1,5,7-tetramethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (306 mg; 0.55 mmol; 1 eq.) in 1,4-dioxane (6 mL) followed by water (604) and the resulting mixture was stirred at room temperature for 16 hours. A 4M solution of HCl in 1,4-dioxane (0.55 mL; 2.21 mmol; 4 eq.) was added and the resulting mixture was stirred at room temperature for 3 hours. Concentration in afforded the title compound (34 mg, quantitative) as an orange solid. 1H NMR (DMSO-d6) δ 9.09 (br s, 1H), 8.76 (br s, 1H), 7.48-7.38 (m, 1H), 7.37-7.17 (m, 2H), 7.06 (t, J=7.1 Hz, 1H), 4.85-4.67 (m, 1H), 4.41 (s, 2H), 3.05 (s, 4H), 2.84 (s, 3H), 2.54 (s, 3H), 2.06 (br s, 2H), 1.90 (s, 6H), 1.87-1.71 (m, 2H). HPLC (max plot) 99.8%, Rt 3.09 min. UPLC/MS: (MS+) 454.5 ([M+H]+).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 3 hours
  2. concentrationConcentration

Sources & evidence

ORD record
ord-7723360e861e409dbe6a263e9c81c005
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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