Dimethylamine → HCID 178484414, compound

HRID 1263963Notes

Reaction equation

HRID 1263963 reaction equation
FC1C([O:8][C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15](=[O:20])[C:14]3=[N:21][NH:22][C:23]2[CH:28]=[CH:27][C:26]([S:29](=[O:32])(=[O:31])[NH2:30])=[CH:25][CH:24]=2)=O)=C(F)C(F)=C(F)C=1F.[CH3:37][NH:38][CH3:39].N1C=CC=CC=1>C(#N)C.C(O)C>[CH3:37][N:38]([CH3:39])[C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:20])[C:14]2=[N:21][NH:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](=[O:32])(=[O:31])[NH2:30])=[CH:25][CH:24]=1)=[O:8]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 1049PyridineHCID 178514750HCID 178514750, compound

Product 1

HCID 178484414HCID 178484414, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

To 100 mg (0.190 mmol) 2-oxo-3[(4-sulfamoyl-phenyl)-hydrazono]-2,3-dihydro-1H-indole-5-carboxylic acid pentafluorophenyl ester in 5 mL acetonitrile was added 50 μL (5.6 M in ethanol, 0.28 mmol) of a solution of dimethylamine and 20 μL (0.25 mmol) of pyridine, and the reaction was stirred overnight. The solution was concentrated, and the resulting solid was triturated with EtOAc to give the title compound as a yellow solid (39 mg, 53%): mp>230° C.; 1H NMR (DMSO-d6): δ 12.71 (s, 1H), 11.22 (s, 1H), 7.75 (d, J=8.8 Hz, 2H), 7.60 (s, 1H), 7.58 (d, J=8.8 Hz, 2H), 7.31 (dd, J=1.7, 8.1 Hz, 1H), 7.23 (s, 2H), 6.93 (d, J=8.0 Hz, 1H), 2.95 (s, 6H); APCI−MS: m/z 386 (m−H). Anal. Calcd for C17H17N5O5S.1/2H2O: C, 51.51; H, 4.58; N, 17.67. Found: C, 51.69; H, 4.25; N, 17.63.

Workup

  1. concentrationThe solution was concentrated
  2. customthe resulting solid was triturated with EtOAc

Sources & evidence

ORD record
ord-68b3fcf00f374a17a288e8a0ff2b16b0
Source dataset
uspto-grants-2003_04
Patent number
US06541503B2

Reaction notes

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