Triethylamine → HCID 68528488, compound

HRID 1932513Notes

Reaction equation

HRID 1932513 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:27]=[CH:26][C:7]([O:8][C:9]2[N:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=3)=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][CH:38]([C:41](O)=[O:42])[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29].C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C>[Cl:24][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[Cl:23])[C:16]([NH:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][C:7]2[CH:26]=[CH:27][C:4]([NH:3][C:41]([CH:38]3[CH2:39][CH2:40][N:35]([C:33]([O:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:34])[CH2:36][CH2:37]3)=[O:42])=[CH:5][CH:6]=2)=[N:14][CH:13]=1)=[O:25]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68526231HCID 68526231, compound

Product 1

HCID 68528488HCID 68528488, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[6-(4-aminophenoxy)pyridin-3-yl]-3,4-dichlorobenzamide dihydrochloride (1.0 g, 2.24 mmol) in DMF (15 mL) were added, piperidine-1,4-dicarboxylic acid mono-t-butyl ester (510 mg, 2.22 mmol), triethylamine (0.94 mL, 6.74 mmol), 1-hydroxybenzotriazole monohydrate (350 mg, 2.29 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (514 mg, 2.68 mmol) under ice cooling. The resulting solution was then stirred under ice cooling for 1 hour, and at room temperature for 17 hours. This reaction solution was concentrated under reduced pressure. The residue was diluted with water and ethyl acetate, whereupon a white powder was precipitated. The white powder was filtered, then washed with water, and subsequently washed with ethyl acetate, to thereby yield 1.04 g of the title compound.

Workup

  1. waitat room temperature for 17 hours
  2. concentrationThis reaction solution was concentrated under reduced pressure
  3. additionThe residue was diluted with water and ethyl acetate, whereupon a white powder
  4. customwas precipitated
  5. filtrationThe white powder was filtered
  6. washwashed with water
  7. washsubsequently washed with ethyl acetate

Sources & evidence

ORD record
ord-31304ad894b64576b14743576562189b
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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