1,4-Dioxane hydrochloride → HCID 122436378, compound

HRID 1479099Notes

Reaction equation

HRID 1479099 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([N:20]1[CH2:34][C:23]2=[C:24]3[N:29]([N:30]=[C:22]2[CH2:21]1)[C:28]([CH3:31])=[C:27]([Cl:32])[C:26]([CH3:33])=[N:25]3)=[O:19])C)(C)(C)C.O1CCOCC1.Cl>C(Cl)Cl>[Cl:32][C:27]1[C:26]([CH3:33])=[N:25][C:24]2[N:29]([N:30]=[C:22]3[CH2:21][N:20]([C:18]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[O:11][CH2:10][CH2:9][NH:7][CH3:6])=[O:19])[CH2:34][C:23]3=2)[C:28]=1[CH3:31]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 89650969HCID 89650969, compound

Product 1

HCID 122436378HCID 122436378, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {2-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-phenoxy]-ethyl}-methyl-carbamic acid tert-butyl ester (1.54 mg; 3.08 mmol; 1 eq.) in a 4M solution of HCl 1,4-dioxane (7.7 mL; 30.8 mmol; 10 eq.) and DCM (25 mL) was stirred at room temperature for 2 hours then concentrated in vacuo. After dilution with DCM, the solution was washed with sat. aq. Na2CO3, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (1.2 g, 89%) as a yellow powder. 1H NMR (DMSO-d6) δ 10.12 (br s, 2H), 7.46-7.35 (m, 1H), 7.35-7.26 (m, 1H), 7.18-7.10 (m, 1H), 7.04 (t, J=7.4 Hz, 1H), 4.85 (d, J=8.3 Hz, 2H), 4.67-4.28 (m, 3H), 4.22-3.74 (m, 4H), 3.62-3.45 (m, 2H), 2.85 (s, 1.5H), 2.81 (s, 1.5H), 2.62 (s, 1.5H), 2.56 (s, 1.5H), 2.34-2.19 (m, 1H), 2.17-1.98 (m, 1H). HPLC (max plot) 94.7%, Rt 2.61 min. UPLC/MS: (MS+) 400.2 ([M+H]+).

Workup

  1. concentrationthen concentrated in vacuo
  2. washAfter dilution with DCM, the solution was washed with sat. aq. Na2CO3
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c59b9758abe64266bd7597e2b86a292e
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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