1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 68526130, compound

HRID 884187Notes

Reaction equation

HRID 884187 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:27]=[CH:26][C:6]([C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=3)=[N:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.[O:30]=[C:31]1[CH2:40][CH2:39][C:38]2[C:33](=[CH:34][CH:35]=[C:36]([CH2:41][N:42]3[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]3)[CH:37]=2)[NH:32]1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C>[O:30]=[C:31]1[CH2:40][CH2:39][C:38]2[C:33](=[CH:34][CH:35]=[C:36]([CH2:41][N:42]3[CH2:43][CH2:44][N:45]([C:21]([C:20]4[CH:24]=[CH:25][C:17]([O:16][C:13]5[N:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]6[CH:26]=[CH:27][C:3]([C:2]([F:28])([F:29])[F:1])=[CH:4][CH:5]=6)=[CH:11][CH:12]=5)=[CH:18][CH:19]=4)=[O:23])[CH2:46][CH2:47]3)[CH:37]=2)[NH:32]1

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68522091HCID 68522091, compoundHCID 68523844HCID 68523844, compound

Product 1

HCID 68526130HCID 68526130, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[5-(4-trifluoromethylbenzoylamino)pyridin-2-yloxy]benzoic acid (4.30 g, 10.7 mmol) in DMF (150 mL) were added 1-(2-oxo-1,2,3,4-tetrahydroquinoline-6-ylmethyl)-piperazine (2.6 g, 10.7 mmol), 1-hydroxybenzotriazole monohydrate (1.64 g, 10.7 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.46 g, 12.8 mmol) under ice cooling, and the resulting solution was stirred for 1 hour under ice cooling and for 17 hours at room temperature. This reaction solution was concentrated under reduced pressure. To the residue was added a saturated sodium bicarbonate solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was recrystallized from ethyl acetate, to thereby yield 5.24 g of the title compound.

Workup

  1. concentrationThis reaction solution was concentrated under reduced pressure
  2. additionTo the residue was added a saturated sodium bicarbonate solution
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ac2353039ea14355bc3beca9a8758e63
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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