Hydrochloric Acid → HCID 71610126, compound

HRID 1479054Notes

Reaction equation

HRID 1479054 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[CH2:25]2)[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>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:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[O:15][CH:12]4[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]4)=[O:23])[CH2:38][C:27]3=2)[C:32]=1[CH3:35]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 89643889HCID 89643889, compound

Product 1

HCID 71610126HCID 71610126, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A 4M solution of HCl in 1,4-dioxane (6.6 mL; 26.4 mmol; 5 eq.) was added to a solution of 4-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (2.78 g; 5.28 mmol; 1 eq.) in 1,4-dioxane (30 mL) and the reaction mixture was stirred at room temperature for 18 hours then concentrated in vacuo. The residue was partitioned between DCM and sat. aq. Na2CO3 and the two phases separated. The organic layer was dried over magnesium sulfate and concentrated in vacuo to afford the title compound (1.78 g, 79%) as a yellow solid. 1H NMR (DMSO-d6) δ 7.46-7.39 (m, 1H), 7.33-7.29 (m, 1H), 7.21-7.19 (m, 1H), 7.07-7.01 (m, 1H), 4.85 (s, 1H), 4.82 (s, 1H), 4.58-4.49 (m, 3H), 2.92-2.76 (m, 2H), 2.84 (s, 1.5H), 2.80 (s, 1.5H), 2.69-2.58 (m, 2H), 2.62 (s, 1.5H), 2.55 (s, 1.5H), 1.93-1.68 (m, 2H), 1.54-1.43 (m, 2H). HPLC (max plot) 92.5%; Rt 2.69 min. UPLC/MS: (MS+) 426.4 ([M+H]+).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was partitioned between DCM and sat. aq. Na2CO3
  3. customthe two phases separated
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6fdd82ac50a640f6b3b07a552ab8557c
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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