Boron tribromide → HCID 23624294, compound

HRID 217307Notes

Reaction equation

HRID 217307 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([Cl:21])=[CH:10][C:11]3[CH2:12]O[CH2:14][C:15]4[C:20]=3[C:19]=2[CH:18]=[CH:17][CH:16]=4)[N:5]=[C:4]([S:22][CH2:23][CH2:24][CH2:25][C:26]([NH2:28])=[O:27])[N:3]=1.B(Br)(Br)Br.O.O.O.O.O.O.O.O.O.[S-2:42].[Na+].[Na+].C(N(C(C)C)C(C)C)C>ClCCl.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:19]3[C:20]4[C:11]([CH2:12][S:42][CH2:14][C:15]=4[CH:16]=[CH:17][CH:18]=3)=[CH:10][C:9]=2[Cl:21])[N:5]=[C:4]([S:22][CH2:23][CH2:24][CH2:25][C:26]([NH2:28])=[O:27])[N:3]=1

Participants

7

Reactant 4

HCID 25134Boron tribromideHCID 73972Sodium sulfide nonahydrateHCID 81531DiisopropylethylamineHCID 25066238HCID 25066238, compound

Product 1

HCID 23624294HCID 23624294, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[4-amino-6-(5-chloro-1H,3H-benzo[de]isochromen-6-yl)-[1,3,5]triazin-2-ylsulfanyl]-butyramide (100 mg, 0.24 mmol) obtained in Example 339 was dissolved in dichloromethane (4 ml) at room temperature. To the solution was added boron tribromide (1.0M in dichloromethane, 0.96 ml) and the resulted suspension was stirred overnight. The mixture was concentrated followed by dilution with N,N-dimethylformamide (6 ml). To the mixture were added sodium sulfide nonahydrate (220 mg, 2.46 mmol) and N-ethyldiisopropylamine (0.2 ml) successively at room temperature for 6 hours. The mixture was diluted with ethyl acetate (100 ml), and washed with water (50 ml, 3 times), brine successively, and then dried over anhydrous sodium sulfate. After removal of inorganic salts by filtration, the filtrate was concentrated. The resulting residue was purified by silica gel thin layer chromatography (developing solvent; dichloromethane/methanol=9:1) to give 4-[4-amino-6-(5-chloro-1H,3H-2-thia-phenalen-6-yl)-[1,3,5]triazin-2-ylsulfanyl]-butyramide (52 mg, 49%) as a yellow solid.

Workup

  1. concentrationThe mixture was concentrated
  2. washwashed with water (50 ml, 3 times), brine successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter removal of inorganic salts
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated
  7. customThe resulting residue was purified by silica gel thin layer chromatography (developing solvent; dichloromethane/methanol=9:1)

Sources & evidence

ORD record
ord-a199bde4d26d4816b3e9fea23c87a7e1
Source dataset
uspto-grants-2012_06
Patent number
US08193351B2

Reaction notes

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