Tris(hydroxymethyl)aminomethane → HCID 10140388, compound

HRID 2250145Notes

Reaction equation

HRID 2250145 reaction equation
[CH2:1]([N:3]([CH2:22][CH3:23])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([NH:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[CH3:15])=[CH:10][CH:9]=1)[CH3:2].[C:24]1([CH2:30][S:31](Cl)(=[O:33])=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O)C(N)(CO)CO.CS(Cl)(=O)=O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:22]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]([N:16]([CH2:17][CH2:18][N:19]([CH3:20])[CH3:21])[S:31]([CH2:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:33])=[O:32])[CH3:15])=[CH:12][CH:13]=1)[CH3:23]

Participants

7

Reactant 4

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 31297Methanesulfonyl chlorideHCID 74740Phenylmethanesulfonyl chlorideHCID 9966914HCID 9966914, compound

Product 1

HCID 10140388HCID 10140388, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 4 ml vial was placed N-{1-[4-(3-Diethylamino-propoxy)-phenyl]-ethyl}-N′,N′-dimethyl-ethane-1,2-diamine (22 mg, 0.07 mmol), phenyl-methanesulfonyl chloride (27 mg, 0.14 mmol), PS-DMAP (93 mg, 1.48 mmol/g), and CH2Cl2 (1.5 ml). The vial was agitated by means of a lab quake shaker for 4 h. To the solution was added PS-Trisamine (100 mg, 3.3 mmol, 3.0 mmol/g) and the reaction was allowed to agitate overnight to scavenge excess methansulfonyl chloride. Filtration, washing with CH2Cl2 and concentrating afforded N-{1-[4-(3-Diethylamino-propoxy)-phenyl]-ethyl}-N-(2-dimethylamino-ethyl)-C-phenyl-methanesulfonamide. Mass spec hit M+1, 476: LCMS>93% @ 230 nm and ELSD.

Workup

  1. stirringto agitate overnight
  2. filtrationFiltration
  3. washwashing with CH2Cl2
  4. concentrationconcentrating

Sources & evidence

ORD record
ord-a465d423941a42e8b14a0b6ec92ae550
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

Loading…