(2-Methoxyethyl)(methyl)amine → HCID 59199293, compound

HRID 2079690Notes

Reaction equation

HRID 2079690 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)[N:9]=[CH:8]2)=O.[CH3:24][O:25][CH2:26][CH2:27][NH:28][CH3:29].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1.C(O)(=O)C>[CH3:24][O:25][CH2:26][CH2:27][N:28]([CH2:1][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)[N:9]=[CH:8]2)[CH3:29]

Participants

6

Reactant 3

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 5049666Sodium triacetoxyborohydrideHCID 59199232HCID 59199232, compound

Product 1

HCID 59199293HCID 59199293, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To the solution of 4-(8-formylquinazolin-2-ylamino)benzenesulfonamide (11 mg, 30 umole) and 2-methoxy-N-methylethanamine (37 ul, 30 umole) in 500 ul of NMP was added a few drops of acetic acid. The reaction solution was stirred at room temperature for overnight. Sodium triacetoxy borohydride (7 mg, 33 umole) was added. The reaction mixture was stirred for 2 hr at ambient temperature. The reductive amination went to completion to give 4-(8-(((2-methoxyethyl)(methyl)amino)methyl)quinazolin-2-ylamino)benzenesulfonamide that was then purified on prep HPLC to give product as powder. ES/MS m/z 402.2 (MH+).

Workup

  1. stirringThe reaction mixture was stirred for 2 hr at ambient temperature

Sources & evidence

ORD record
ord-67cb58c2d1d742abae92280998e83f2d
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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