Isoamylamine → HCID 10324630, compound

HRID 969478Notes

Reaction equation

HRID 969478 reaction equation
[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][NH2:5].ON1C2C=CC=CC=2N=N1.[CH3:17][N:18]([CH2:28][C:29]1[CH:30]=[C:31]([C:35]2[CH:40]=[CH:39][C:38]([NH:41][C:42]3[CH:50]=[CH:49][CH:48]=[CH:47][C:43]=3[C:44](O)=[O:45])=[CH:37][CH:36]=2)[CH:32]=[CH:33][CH:34]=1)[C:19](=[O:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].CCN=C=NCCCN(C)C.Cl>ClCCl.C(OCC)(=O)C>[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][NH:5][C:44](=[O:45])[C:43]1[CH:47]=[CH:48][CH:49]=[CH:50][C:42]=1[NH:41][C:38]1[CH:37]=[CH:36][C:35]([C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([CH2:28][N:18]([CH3:17])[C:19](=[O:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:30]=2)=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 7894IsoamylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10004335HCID 10004335, compound

Product 1

HCID 10324630HCID 10324630, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

95 mg (1.1 mmol) of 3-methylbutylamine and 160 mg (1.2 mmol) of 1-hydroxybenzotriazole are successively added to a solution of 500 mg (1.1 mmol) of 2-{3′-[(methyloctanoylamino)methyl]biphenyl-4-ylamino}benzoic acid (Example 6) in 15 ml of dichloromethane. The reaction medium is cooled to 0° C. and 230 mg (1.2 mmol) of EDCl are added portionwise. The reaction medium is stirred from 0° C. to room temperature over 6 hours, diluted with ethyl acetate, washed with water and extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with an 80/20 heptane/ethyl acetate mixture. 530 mg of N-(3-methylbutyl)-2-{3′-[(methyloctanoylamino)methyl]biphenyl-4-ylamino}benzamide are obtained in the form of a yellow oil, in a yield of 93%.

Workup

  1. washwashed with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with an 80/20 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-0201d628524b4839b7563620b42b64f6
Source dataset
uspto-grants-2007_12
Patent number
US07307078B2

Reaction notes

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