Aluminium lithium hydride → HCID 67513311, compound

HRID 339714Notes

Reaction equation

HRID 339714 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[C:17]([O:18][CH3:19])=[CH:16][C:15]([O:20][CH3:21])=[CH:14][C:13]=1[NH:22][C:23]1[C:24]([NH:33][S:34]([C:37]2[CH:47]=[CH:46][C:40]([C:41]([N:43]([CH3:45])[CH3:44])=O)=[CH:39][CH:38]=2)(=[O:36])=[O:35])=[N:25][C:26]2[C:31]([N:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2>C1COCC1>[CH3:44][N:43]([CH2:41][C:40]1[CH:39]=[CH:38][C:37]([S:34]([NH:33][C:24]2[C:23]([NH:22][C:13]3[CH:14]=[C:15]([O:20][CH3:21])[CH:16]=[C:17]([O:18][CH3:19])[C:12]=3[O:11][CH2:10][CH2:9][CH2:8][OH:7])=[N:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=2)(=[O:35])=[O:36])=[CH:47][CH:46]=1)[CH3:45]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 56966113HCID 56966113, compound

Product 1

HCID 67513311HCID 67513311, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A total of 4 equivalents of LiAlH4, dissolved in THF, are added to 200 mg of 4-{3-[2-(3-hydroxypropoxy)-3,5-dimethoxyphenylamino]quinoxalin-2-ylsulfamoyl}-N,N-dimethylbenzamide, dissolved in about 10 ml of THF, at 0° C. (ice bath) in a multinecked flask which has been dried by heating, and the mixture is stirred at RT until the starting material has reacted virtually completely (several hours, HPLC check). The reaction mixture is quenched by addition of 5 ml of methanol. The solution is acidified until everything dissolves, evaporated somewhat and purified by preparative HPLC on silica gel RP18 (acetonitrile, water), giving 75 mg of 4-dimethylaminomethyl-N-{3-[2-(3-hydroxypropoxy)-3,5-dimethoxyphenylamino]quinoxalin-2-yl}benzenesulfonamide as yellow solid (yield 36%); MS-FAB (M+H+)=568.2; Rf (polar method): 1.85 min.

Workup

  1. customhas been dried
  2. temperatureby heating
  3. customhas reacted virtually completely (several hours, HPLC check)
  4. customThe reaction mixture is quenched by addition of 5 ml of methanol
  5. dissolutiondissolves
  6. customevaporated somewhat
  7. custompurified by preparative HPLC on silica gel RP18 (acetonitrile, water)

Sources & evidence

ORD record
ord-c010f607b0ff48dbb782ac72cfd2a5f7
Source dataset
uspto-grants-2014_11
Patent number
US08895559B2

Reaction notes

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