1,2-Dichloroethane → HCID 447018, compound

HRID 1883659Notes

Reaction equation

HRID 1883659 reaction equation
F[C:2](F)(F)C(O)=O.[NH2:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=1[CH2:18][NH:19][C:20](=[O:23])[CH2:21]C.C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:43][N:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=[C:45]1[CH2:53][NH:54][CH3:55].C(Cl)CCl>CN(C=O)C>[NH2:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](=[O:15])[N:54]([CH3:55])[CH2:53][C:45]2[N:44]([CH3:43])[C:52]3[C:47]([CH:46]=2)=[CH:48][CH:49]=[CH:50][CH:51]=3)=[CH:11][C:10]=1[CH2:18][N:19]([CH3:2])[C:20](=[O:23])[CH3:21]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amineHCID 69758844HCID 69758844, compound

Product 1

HCID 447018HCID 447018, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-amino-3-[(N-methylacetylamino)methyl]benzoic acid trifluoro acetate (0.73 g, 2.17 mmole), from Procedure 3, in DMF (20 mL) at RT was added diisopropylethyl amine (0.83 ml, 4.78 mmole), HOBt (0.32 g, 2.39 mmole), 1-methyl-2-(methylaminomethyl)indole (0.40 g, 2.39 mmole) and finally EDC (0.45 g, 2.39 mmole). After 12 hr, the reaction contents were poured onto H2O (100 mL) and extracted with EtOAc (2×100 mL). The organic phases were combined and sequentially washed with H2O (100 mL) and brine. Drying over Na2SO4 and purification on silica (CHCl3/CH3OH. 95:5) afforded the title compound (0.73 g, 89%) as a light yellow solid: MS (ES) m/e 379 (M+H)+.

Workup

  1. customthe reaction contents
  2. additionwere poured onto H2O (100 mL)
  3. extractionextracted with EtOAc (2×100 mL)
  4. washsequentially washed with H2O (100 mL) and brine
  5. dry with materialDrying over Na2SO4 and purification on silica (CHCl3/CH3OH. 95:5)

Sources & evidence

ORD record
ord-33d925b6836b485c905a9ace735666d9
Source dataset
uspto-grants-2004_07
Patent number
US06762201B1

Reaction notes

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