Hydrochloric Acid → HCID 178464044, compound

HRID 1382537Notes

Reaction equation

HRID 1382537 reaction equation
[CH2:1]([N:3]([CH2:30][CH3:31])[CH2:4][CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][C:11]([NH:15][CH2:16][CH2:17][NH:18]C(=O)O)=[C:10]3[S:22][C:23]4[CH:28]=[C:27]([OH:29])[CH:26]=[CH:25][C:24]=4[C:8]([C:9]=23)=[N:7]1)[CH3:2].[ClH:32]>C(O)C>[ClH:32].[ClH:32].[ClH:32].[NH2:18][CH2:17][CH2:16][NH:15][C:11]1[CH:12]=[CH:13][C:14]2[N:6]([CH2:5][CH2:4][N:3]([CH2:30][CH3:31])[CH2:1][CH3:2])[N:7]=[C:8]3[C:24]4[CH:25]=[CH:26][C:27]([OH:29])=[CH:28][C:23]=4[S:22][C:10]=1[C:9]=23

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178464045HCID 178464045, compound

Product 1

HCID 178464044HCID 178464044, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
3 °C

Procedure

To an ice-cold solution of 29.4 g (59.1 mmol) of [2-[[2-[2-(diethylamino)ethyl]-8-hydroxy-2H-[1]benzothiopyrano[4,3,2-cd]indazol-5-yl]amino]ethyl]-carbamic acid; 1,1-dimethylethyl ester and 800 mL of absolute ethyl alcohol was slowly bubbled anhydrous hydrogen chloride until the temperature reached 12° C. The mixture was cooled to 3° C., and the bubbling process was repeated three times, then the mixture was warmed to 25° C. After stirring overnight, the solids were collected by filtration then stirred for 30 minutes at 5° C. with a solution of 250 mL of water and 800 mL of ethyl alcohol. The mixture was diluted with an additional 250 mL of ethyl alcohol and stirred at 5° C. for 5 hr, then at -5° C. for 30 minutes. The solids were collected by filtration, washed successively with diethyl ether then hexane, and dried over phosphorus pentoxide at 2 mm/40° C./2 hr then at 2 mm/25° C./48 hr to give 27.6 g (90.5%) of 4 as the trihydrochloride salt and solvated with 0.5 equivalents of water, mp 260°-264° C. (dec), 99.4% pure by HPLC.

Workup

  1. customreached 12° C
  2. temperaturethe mixture was warmed to 25° C
  3. filtrationthe solids were collected by filtration
  4. stirringthen stirred for 30 minutes at 5° C. with a solution of 250 mL of water and 800 mL of ethyl alcohol
  5. additionThe mixture was diluted with an additional 250 mL of ethyl alcohol
  6. stirringstirred at 5° C. for 5 hr
  7. waitat -5° C. for 30 minutes
  8. filtrationThe solids were collected by filtration
  9. washwashed successively with diethyl ether
  10. dry with materialhexane, and dried over phosphorus pentoxide at 2 mm/40° C./2 hr

Sources & evidence

ORD record
ord-50e532dff4054ed1a1451603902f0594
Source dataset
uspto-grants-1989_02
Patent number
US04806654

Reaction notes

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