Dimethylamine → HCID 59335117, compound

HRID 1517962Notes

Reaction equation

HRID 1517962 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C:13]2[CH:21]=[C:20]3[C:16]([C:17]([C:23](O)=[O:24])=[CH:18][N:19]3[CH3:22])=[CH:15][CH:14]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH:26]([N:29](C(C)C)[CH2:30]C)(C)C.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.F[B-](F)(F)F.CNC>CN(C)C=O.O1CCCC1.C(OCC)(=O)C.O>[CH3:26][N:29]([CH3:30])[C:23]([C:17]1[C:16]2[C:20](=[CH:21][C:13]([NH:12][S:9]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)(=[O:10])=[O:11])=[CH:14][CH:15]=2)[N:19]([CH3:22])[CH:18]=1)=[O:24]

Participants

9

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68413742HCID 68413742, compound

Product 1

HCID 59335117HCID 59335117, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

300 mg 6-(3,5-dichloro-phenylsulphonylamino)-1-methyl-1H-indole-3-carboxylic acid are dissolved in 2 ml dimethylformamide, combined with 319 μl N,N-diisopropyl-N-ethyl-amine and 241 mg O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium-tetrafluoroborate (TBTU) and stirred for 15 minutes at ambient temperature. 751 μl of a 2 M solution of dimethylamine in tetrahydrofuran are added and the mixture is stirred overnight at ambient temperature. Then it is divided between water and ethyl acetate, the aqueous phase is extracted with ethyl acetate and the combined organic phases are dried on magnesium sulphate. The solvents are eliminated in vacuo.

Workup

  1. stirringthe mixture is stirred overnight at ambient temperature
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. customthe combined organic phases are dried on magnesium sulphate

Sources & evidence

ORD record
ord-a2be4ab193fa4d67816b453f5be5b73a
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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