Hydrochloric Acid → 6-chloro-5,7-dimethyl-2,3-dihydro-1H-2,4,7a,8-tetraaza-cyclopenta[a]indene hydrochloride

HRID 1478990Notes

Reaction equation

HRID 1478990 reaction equation
Cl.C(OC([N:9]1[CH2:23][C:12]2=[C:13]3[N:18]([N:19]=[C:11]2[CH2:10]1)[C:17]([CH3:20])=[C:16]([Cl:21])[C:15]([CH3:22])=[N:14]3)=O)(C)(C)C.CC(OC)(C)C>CC(O)=O>[ClH:21].[Cl:21][C:16]1[C:15]([CH3:22])=[N:14][C:13]2[N:18]([N:19]=[C:11]3[CH2:10][NH:9][CH2:23][C:12]3=2)[C:17]=1[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15413tert-Butyl methyl etherHCID 896439786-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid tert-butyl ester

Product 1

HCID 896439086-chloro-5,7-dimethyl-2,3-dihydro-1H-2,4,7a,8-tetraaza-cyclopenta[a]indene hydrochlorideYield 199.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Aq. 32% HCl (1.14 mL; 11.62 mmol; 3 eq.) was added to a suspension of 6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid tert-butyl ester (1.25 g; 3.87 mmol; 1 eq.) in AcOH (6.25 mL) and the resulting mixture was stirred at room temperature for 2 hours then poured into MTBE (40 mL). The precipitate was filtered off, washed with MTBE (3×) and dried to afford the title compound (1 g, 100%) as an off-white solid. 1H NMR (DMSO-d6) δ 10.55 (s, 2H), 4.57-4.52 (m, 4H), 2.83 (s, 3H), 2.61 (s, 3H). HPLC (max plot) 100.0%; Rt 1.38 min. UPLC/MS: (MS+) 222.9 ([M+H]+).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with MTBE (3×)
  3. customdried

Sources & evidence

ORD record
ord-e39329ba86ed45388c29ff6affa8c865
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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