Dimethylformamide → HCID 58775951, compound

HRID 1715340Notes

Reaction equation

HRID 1715340 reaction equation
CCN=C=N[CH2:6][CH2:7][CH2:8][N:9]([CH3:11])[CH3:10].[Cl:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([C:22]([OH:24])=O)=[CH:16]2.[CH:25]1[CH:26]=[CH:27][C:28]2[N:33](O)N=N[C:29]=2[CH:30]=1.CCN([CH2:40][CH3:41])CC.[CH3:42]N(C=O)C>CN(C1C=CN=CC=1)C.O>[CH:8]1([N:9]([CH2:10][C:25]2[CH:26]=[CH:27][C:28]([NH:33][C:22]([C:17]3[NH:18][C:19]4[C:15]([CH:16]=3)=[CH:14][C:13]([Cl:12])=[CH:21][CH:20]=4)=[O:24])=[CH:29][CH:30]=2)[CH3:11])[CH2:7][CH2:6][CH2:41][CH2:40][CH2:42]1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 826935-Chloro-1H-indole-2-carboxylic acid

Product 1

HCID 58775951HCID 58775951, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

EDCI (0.33 mmol, 0.07 g) was added in one portion to a suspension of Compound 14c (0.25 mmol, 0.05 g), 5-chloro-1H-indole-2-carboxylic acid Compound 14d (0.22 mmol, 0.04 g) and HOBt (0.22 mmol, 0.03 g) in DMF (5.0 mL) at 0° C. The resulting suspension was warmed to r.t. and then a crystal of DMAP and Et3N (0.65 mmol, 0.1 mL) was added and the reaction mixture was stirred overnight. The resulting orange-yellow suspension was poured in water and was extracted with EtOAc (25 mL). The organic layer was washed with water (2×20 mL) followed by 5% NaOH solution (10 mL) and brine. The organic layer was separated, dried over Na2SO4 and filtered. The solvent was removed in vacuo and the resulting residue was purified by preparative TLC (15:1 CH2Cl2/MeOH) to yield 5-chloro-1H-indole-2-carboxylic acid {4-[(cyclohexyl-methyl-amino)-methyl]-phenyl}-amide Compound 14e (0.06 g, 68%) as a pale yellow solid. MS m/e 396 (M+H, 100%).

Workup

  1. extractionwas extracted with EtOAc (25 mL)
  2. washThe organic layer was washed with water (2×20 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customthe resulting residue was purified by preparative TLC (15:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-2d6166435ef041eb8d9187f80b6e9819
Source dataset
uspto-grants-2010_09
Patent number
US07799824B2

Reaction notes

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