N-(2-Dimethylamino-1-methyl-ethyl)-benzene-1,4-diamine → HCID 178426958, compound

HRID 2352868Notes

Reaction equation

HRID 2352868 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:30].[CH3:31][N:32]([CH3:44])[CH2:33][CH:34]([NH:36][C:37]1[CH:42]=[CH:41][C:40]([NH2:43])=[CH:39][CH:38]=1)[CH3:35]>C1COCC1>[CH3:44][N:32]([CH3:31])[CH2:33][CH:34]([NH:36][C:37]1[CH:38]=[CH:39][C:40]([NH:43][CH:2]=[C:3]2[C:11]3[C:6](=[CH:7][C:8]([C:12]([C:14]4[CH:15]=[C:16]([NH:20][C:21]([C:23]5[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=5)=[O:22])[CH:17]=[CH:18][CH:19]=4)=[O:13])=[CH:9][CH:10]=3)[NH:5][C:4]2=[O:30])=[CH:41][CH:42]=1)[CH3:35]

Participants

4

Reactant 2

HCID 68698652N-(2-Dimethylamino-1-methyl-ethyl)-benzene-1,4-diamineHCID 178426964HCID 178426964, compound

Product 1

HCID 178426958HCID 178426958, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 60, 116 mg, 0.288 mmol) and THF (2 mL). To the resulting solution was added N-(2-Dimethylamino-1-methyl-ethyl)-benzene-1,4-diamine (prepared below, 61.4 mg, 0.314 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature. Hexanes were added to the reaction mixture and the reaction mixture was vacuum filtered. The black solid collected was set aside. The filtrate was then concentrated in vacuo and then redissolved into EtOAc and then Hexanes were added causing a precipitate to form. The precipitate was then filtered and washed with ˜1 mL of i-prOH yielding 40% (0.067 g, 0.116 mmol) of the title compound.

Workup

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. customThe black solid collected
  5. concentrationThe filtrate was then concentrated in vacuo
  6. dissolutionredissolved into EtOAc
  7. additionHexanes were added
  8. customto form
  9. filtrationThe precipitate was then filtered

Sources & evidence

ORD record
ord-a6c607bc79664d52963f5cbfe28ec2dc
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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