Hydrochloric Acid → N-(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-N'-(6-hydroxyhexyl)succinamide

HRID 1797323Notes

Reaction equation

HRID 1797323 reaction equation
[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[Cl:19][C:20]1[CH:21]=[C:22]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[NH:42][C:43](=[O:49])[CH2:44][CH2:45][C:46](O)=[O:47])[CH:23]=[CH:24][C:25]=1[C:26](=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33].[NH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][OH:57].Cl>C1COCC1>[Cl:19][C:20]1[CH:21]=[C:22]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[NH:42][C:43](=[O:49])[CH2:44][CH2:45][C:46]([NH:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][OH:57])=[O:47])[CH:23]=[CH:24][C:25]=1[C:26](=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 199606-Amino-1-hexanolHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 9845903N-[2-[3-Chloro-4-(2-methylbenzoyl)-phenylamino]phenyl]-succinamic Acid

Product 1

HCID 22174461N-(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-N'-(6-hydroxyhexyl)succinamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium chloride (DMT-MM) (138 mg, 0.50 mmol) was added to a solution of N-(2-{[3-chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-succinamic acid (200 mg, 0.46 mmol) (disclosed in WO 01/05746) and 6-aminohexanol (60 mg, 0.51 mmol) in THF (4.0 mL). The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was poured into 1 N HCl (aq.) and was extracted with EtOAc (×2). The combined organic phases were washed with water, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using DCM/MeOH/NH3(aq.) 95:5:0.5 as the eluent to afford the title compound as a yellow solid.

Workup

  1. extractionwas extracted with EtOAc (×2)
  2. washThe combined organic phases were washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-00288187bc6240e785a4a6d96f6c5ec9
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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