Triethylamine → HCID 58923881, compound

HRID 1364078Notes

Reaction equation

HRID 1364078 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].Cl.Cl.[CH3:8][C:9]1[N:22]=[C:21]([NH2:23])[C:12]2[N:13]=[C:14]3[CH2:20][NH:19][CH2:18][CH2:17][CH2:16][N:15]3[C:11]=2[C:10]=1[CH3:24].C(N(CC)CC)C>CN(C=O)C>[CH3:8][C:9]1[N:22]=[C:21]([NH2:23])[C:12]2[N:13]=[C:14]3[CH2:20][N:19]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:18][CH2:17][CH2:16][N:15]3[C:11]=2[C:10]=1[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66958527HCID 66958527, compound

Product 1

HCID 58923881HCID 58923881, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methanesulfonyl chloride (198 mg, 1.73 mmol) was added to a solution of 3,4-dimethyl-7,8,9,10-tetrahydro-6H-pyrido[3′,4′:4,5]imidazo[1,2-a][1,4]diazepin-1-amine dihydrochloride (400 mg, 1.31 mmol) and triethylamine (350 mg, 3.46 mmol) in DMF (250 mL) and stirred overnight at ambient temperature. The reaction mixture was concentrated under reduced pressure and adsorbed onto silica gel. The material was purified by column chromatography on silica gel, concentrated under reduced pressure, dissolved in dimethyl sulfoxide (DMSO), and purified by reverse phase prep HPLC (eluting with 0.5% formic acid in water/0.5% formic acid in acetonitrile in a 10-minute gradient from 5:95 to 95:5) using a HPLC purification system obtained from Shimadzu corporation (based in Kyoto, Japan) to afford 135 mg of 3,4-dimethyl-9-(methylsulfonyl)-7,8,9,10-tetrahydro-6H-pyrido[3′,4′:4,5]imidazo[1,2-a][1,4]diazepin-1-amine. HRMS (EI) calcd for C13H19N5O2S 310.1338, found 310.1346.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe material was purified by column chromatography on silica gel
  3. concentrationconcentrated under reduced pressure
  4. dissolutiondissolved in dimethyl sulfoxide (DMSO)
  5. custompurified by reverse phase prep HPLC (
  6. washeluting with 0.5% formic acid in water/0.5% formic acid in acetonitrile in a 10-minute gradient from 5:95 to 95:5)
  7. customa HPLC purification system

Sources & evidence

ORD record
ord-aedf62e9667942bbaf529bec55b251ce
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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