Hydrochloric Acid → HCID 117734879, compound

HRID 1479048Notes

Reaction equation

HRID 1479048 reaction equation
Cl.C(OC([N:9]1[CH2:22][C:12]2=[C:13]3[N:18]([N:19]=[C:11]2[CH2:10]1)[C:17]([CH3:20])=[C:16]([Cl:21])[CH:15]=[N:14]3)=O)(C)(C)C>CC(O)=O.C(Cl)Cl>[Cl:21][C:16]1[CH:15]=[N:14][C:13]2[N:18]([N:19]=[C:11]3[CH2:10][NH:9][CH2:22][C:12]3=2)[C:17]=1[CH3:20]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 117734673HCID 117734673, compound

Product 1

HCID 117734879HCID 117734879, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A 32% solution of HCl (0.14 mL) was added to a solution of 6-chloro-7-methyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid tert-butyl ester (140 mg; 0.44 mmol; 1 eq.) in AcOH (0.5 mL) and the reaction mixture was stirred at room temperature for 16 hours. The solution was diluted with DCM, washed with 1M NaOH (2×), dried over sodium sulfate and concentrated in vacuo to afford the title compound (80 mg, 86%) as a yellow solid. 1H NMR (DMSO-d6) δ 8.48 (s, 1H), 4.12-4.03 (m, 4H), 3.73-3.57 (m, 1H), 2.80 (s, 3H). HPLC (max plot) 99.6%, Rt 1.33 min. UPLC/MS: (MS+) 209.1 ([M+H]+).

Workup

  1. washwashed with 1M NaOH (2×)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3343da2a93cc4594a322f6d4c25cdad3
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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