Dimethylamine, hydrochloride → HCID 118676294, compound

HRID 523045Notes

Reaction equation

HRID 523045 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[C:14]3[C:15](=[O:23])[O:16][C:17]([CH3:22])([C:19](O)=[O:20])[CH2:18][C:13]=3[N:12]=[CH:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH3:24][N:25](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:26].[B-](F)(F)(F)F.Cl.CNC.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:24][N:25]([CH3:26])[C:19]([C:17]1([CH3:22])[O:16][C:15](=[O:23])[C:14]2[N:10]([C:4]3[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:2]([Cl:1])[CH:3]=3)[CH:11]=[N:12][C:13]=2[CH2:18]1)=[O:20]

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118676292HCID 118676292, compound

Product 1

HCID 118676294HCID 118676294, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 50 mg (0.15 mmol) of 44 in 2 mL of DMF is added 58 mg (0.18 mmol) of TBTU, 15 mg (0.18 mmol) of dimethylamine hydrochloride and 0.03 mL (0.2 mmol) of iPr2NEt. The mixture is stirred for 48 h, diluted with 50 mL of EtOAc, and washed twice with 20 mL of H2O and once with 20 mL of brine. The organic phase is dried with MgSO4, filtered, concentrated, and purified twice by preparative TLC (100% EtOAc) to give 22 mg (0.06 mmol) of 46.

Workup

  1. washwashed twice with 20 mL of H2O and once with 20 mL of brine
  2. dry with materialThe organic phase is dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified twice by preparative TLC (100% EtOAc)

Sources & evidence

ORD record
ord-25e5fe1b9e5247d5bccf79f69089d743
Source dataset
uspto-grants-2016_05
Patent number
US09334285B2

Reaction notes

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