Hydrochloric Acid → HCID 89662793, compound

HRID 1479047Notes

Reaction equation

HRID 1479047 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)[CH:17]=[C:16]([Cl:20])[C:15]([CH3:21])=[N:14]3)=O)(C)(C)C>CC(O)=O.C(Cl)Cl>[Cl:20][C:16]1[C:15]([CH3:21])=[N:14][C:13]2[N:18]([N:19]=[C:11]3[CH2:10][NH:9][CH2:22][C:12]3=2)[CH:17]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 896496937H-Pyrrolo[3′,4′:3,4]pyrazolo[1,5-a]pyrimidine-8(9H)-carboxylic acid, 3-chloro-2-methyl-, 1,1-dimethylethyl ester

Product 1

HCID 89662793HCID 89662793, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A 32% solution of HCl (1.79 mL) was added to a solution of 6-chloro-5-methyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid tert-butyl ester (1.70 g; 5.51 mmol; 1 eq.) in AcOH (5.8 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 (900 mg, 78%) as a yellow solid. 1H NMR (DMSO-d6) δ 9.37 (s, 1H), 4.09-3.98 (m, 4H), 3.70-3.53 (m, 1M), 2.55 (s, 3H). HPLC (max plot) 99.8%, Rt 1.20 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-a393b62ad14c49ba9d459633b913a80f
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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