Methanol → HCID 178419254, compound

HRID 1382534Notes

Reaction equation

HRID 1382534 reaction equation
[CH2:1]([N:3]([CH2:38][CH3:39])[CH2:4][CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][C:11]([NH:15][CH2:16][CH2:17][N:18]3[C:26](=[O:27])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]3=[O:28])=[C:10]3[S:29][C:30]4[CH:35]=[C:34]([O:36]C)[CH:33]=[CH:32][C:31]=4[C:8]([C:9]=23)=[N:7]1)[CH3:2].B(Br)(Br)[Br:41].CO>ClCCl>[BrH:41].[BrH:41].[CH2:38]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][C:11]([NH:15][CH2:16][CH2:17][N:18]3[C:19](=[O:28])[C:20]4[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:26]3=[O:27])=[C:10]3[S:29][C:30]4[CH:35]=[C:34]([OH:36])[CH:33]=[CH:32][C:31]=4[C:8]([C:9]=23)=[N:7]1)[CH3:39]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromide2×HCID 144067742-[2-[[2-[2-(Diethylamino)ethyl]-8-methoxy-2H-[1]benzothiopyrano[4,3,2-cd]indazol-5-yl]amino]ethyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 178419254HCID 178419254, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 25° C. solution of 324.1 g (0.598 mol) of 2-[2-[[2-[2-(diethylamino)ethyl]-8-methoxy-2H-[1]benzothiopyrano[4,3,2-cd]indazol-5-yl]amino]ethyl]-1H-isoindole-1,3(2H)-dione (2) in 7.45 L of dichloromethane was treated dropwise over 2 hr with 2.1 L (2.1 mol) of a 1M solution of boron tribromide in dichloromethane. The mixture was heated at reflux for 6.75 hr, treated with an additional 300 mL (0.3 mol) of boron tribromide solution, then further heated overnight. The refluxing mixture was treated cautiously with 1.86 L of methanol, heated an additional 12 hr, then cooled and stirred for 3 hr in an ice bath. The solids were collected by filtration, washed successively with dichloromethane and hexane, then dried at 220 mm/45° C./20 hr to give 291.8 g (70.8%) of 3, mp 232.5°- 234° C., 98.9% pure by HPLC.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6.75 hr
  3. temperaturefurther heated overnight
  4. temperatureheated an additional 12 hr
  5. temperaturecooled
  6. filtrationThe solids were collected by filtration
  7. washwashed successively with dichloromethane and hexane
  8. customdried at 220 mm/45° C./20 hr

Sources & evidence

ORD record
ord-720248306ade409c97e9af510acf7812
Source dataset
uspto-grants-1989_02
Patent number
US04806654

Reaction notes

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