Diisopropylethylamine → 5-cyano-6-ethoxy-3-nitro-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)picolinamide

HRID 2407839Notes

Reaction equation

HRID 2407839 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N+:15]([O-:17])=[O:16])[C:6]([C:12]([OH:14])=O)=[N:7][C:8]=1[O:9][CH2:10][CH3:11])#[N:2].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.Cl.Cl.[N:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[C:50]1[S:51][C:52]([CH2:55][N:56]2[CH2:61][CH2:60][CH:59]([CH2:62][NH2:63])[CH2:58][CH2:57]2)=[CH:53][N:54]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O.O>[C:1]([C:3]1[CH:4]=[C:5]([N+:15]([O-:17])=[O:16])[C:6]([C:12]([NH:63][CH2:62][CH:59]2[CH2:60][CH2:61][N:56]([CH2:55][C:52]3[S:51][C:50]([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][N:44]=4)=[N:54][CH:53]=3)[CH2:57][CH2:58]2)=[O:14])=[N:7][C:8]=1[O:9][CH2:10][CH3:11])#[N:2]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 585043075-cyano-6-ethoxy-3-nitropicolinic AcidHCID 66989375(1-((2-(Pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methanamine Trihydrochloride

Product 1

HCID 585042275-cyano-6-ethoxy-3-nitro-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)picolinamideYield 47.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of the compound prepared in Example 447 (94 mg) and 1-hydroxybenzotriazole hydrate (67 mg) in N,N-dimethylformamide (2.5 mL) at ambient temperature was added 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (84 mg). The resulting solution was stirred at ambient temperature for 40 minutes, and then the compound prepared in Example 214 (189 mg) was added, followed immediately by N,N-diisopropylethylamine (0.35 mL). The resulting mixture was stirred at ambient temperature for 1 hr 50 minutes, and then diluted with water (25 mL). After stirring for 30 minutes, the resulting precipitate was collected by filtration, washed with a small amount of water, and dried under vacuum to provide the title compound (95 mg) with the following physical data.

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature for 1 hr 50 minutes
  2. stirringAfter stirring for 30 minutes
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with a small amount of water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-e740be7d23d4433b890791fd5a6af99f
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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