Hydrochloric Acid → (10RS)-10-amino-10-(4-phenylbutyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride

HRID 2393400Notes

Reaction equation

HRID 2393400 reaction equation
C([NH:4][C:5]1([CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:17]2[N:16]3[CH:18]=[CH:19][N:20]=[C:15]3[C:14](=[O:21])[NH:13][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2)(=O)C.[ClH:32]>>[ClH:32].[NH2:4][C:5]1([CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:17]2[N:16]3[CH:18]=[CH:19][N:20]=[C:15]3[C:14](=[O:21])[NH:13][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 18975476(10 RS)-10-acetamido-10-(4-phenylbutyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 18975399(10RS)-10-amino-10-(4-phenylbutyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride

Procedure

A suspension of 200 mg of (10 RS)-10-acetamido-10-(4-phenylbutyl)-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one in 15 ml of 6N hydrochloric acid is refluxed for 2 hours. The reaction medium is cooled and filtered on a sinter funnel. The solid obtained is crystallized from 5 ml of ethanol. 85 mg of (10RS)-10-amino-10-(4-phenylbutyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride are thus obtained [1H NMR spectrum: (300 MHz, (CD3)2SO-d6 ; δ in ppm): 0.65 (mt, 2H: CH2); 1.38 (mt, 2H: CH2); 2.35 (mt, 2H: hetero-CH2); from 2.50 to 2.80 (mt, 2H: ArCH2); 6.95 (d, J=7.5 Hz, 2H: aromatic ortho H of the phenyl); from 7.00 to 7.20 (mt, 3H: aromatic meta and para H of the phenyl); 7.52 and 7.58 (2 t, J=8 Hz, 1H each: H 7 and H 8); 7.72 and 8.68 (2 broad s, 1H each: H of the imidazole); 7.92 and 8.02.(2 broad d, J=8 Hz), 1H each: H 6 and H 9); 9.48 (mult., 3H: NH2+Cl-); 12.72 (broad s, 1H: NH 5)].

Workup

  1. temperatureis refluxed for 2 hours
  2. temperatureThe reaction medium is cooled
  3. filtrationfiltered on a sinter funnel
  4. customThe solid obtained
  5. customis crystallized from 5 ml of ethanol

Sources & evidence

ORD record
ord-20367be0b00649fdb6b69a46f7553582
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

Loading…