Triethylamine → HCID 10367633, compound

HRID 1986658Notes

Reaction equation

HRID 1986658 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[CH:4]=[C:3]1[C:14]([OH:16])=O.CCN(CC)CC.[NH2:24][C:25]1[C:26]([O:40][CH3:41])=[C:27]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])[CH:28]=[C:29]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:30]=1>>[C:31]([C:29]1[CH:28]=[C:27]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])[C:26]([O:40][CH3:41])=[C:25]([NH:24][C:14]([C:3]2[N:2]([CH3:1])[C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][C:9]=3[N+:11]([O-:13])=[O:12])=[O:16])[CH:30]=1)([CH3:34])([CH3:32])[CH3:33]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamideHCID 577224441-Methyl-7-nitroindole-2-carboxylic acid

Product 1

HCID 10367633HCID 10367633, compoundYield 87%

Procedure

A suspension of 1-methyl-7-nitroindole-2-carboxylic acid (220 mg, 1 mmol) in 5 mL of SO2Cl was heated at reflux for 3 h to give a yellow solution. The excess SO2Cl was removed by distillation and the resulting yellow solid was dissolved in 5 mL of dry THF. Et3N (0.21 mL, 1.5 mmol) and N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide (327 mg, 1.2 mmol) were added successively and the mixture was stirred 12 h. The reaction mixture was extracted with EtOAc to give 410 mg (87%) of 1-methyl-7-nitroindole-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. customto give a yellow solution
  4. customThe excess SO2Cl was removed by distillation
  5. dissolutionthe resulting yellow solid was dissolved in 5 mL of dry THF
  6. extractionThe reaction mixture was extracted with EtOAc

Sources & evidence

ORD record
ord-5cc62054f5ab461a901888daa79f32c1
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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