m-Toluidine → HCID 71623040, compound

HRID 2174228Notes

Reaction equation

HRID 2174228 reaction equation
CCN=C=NCCCN(C)C.Cl.O.ON1C2C=CC=CC=2N=N1.[CH:24]1([NH:30][C:31]2[C:36]([C:37]([O:39]CC)=O)=[CH:35][N:34]=[C:33]([NH:42][C:43]([NH:45][CH2:46][CH3:47])=[O:44])[CH:32]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.[NH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([CH3:55])[CH:50]=1>CN(C=O)C.O>[CH:24]1([NH:30][C:31]2[C:36]([C:37]([NH:48][C:49]3[CH:50]=[C:51]([CH3:55])[CH:52]=[CH:53][CH:54]=3)=[O:39])=[CH:35][N:34]=[C:33]([NH:42][C:43]([NH:45][CH2:46][CH3:47])=[O:44])[CH:32]=2)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

7

Reactant 4

HCID 7934m-ToluidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 89650220HCID 89650220, compound

Product 1

HCID 71623040HCID 71623040, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

EDCI.HCl (1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, 0.092 g, 0.480 mmol) and 1-hydroxybenzotriazole monohydrate (0.073 g, 0.480 mmol) were added to a stirred solution of ethyl 4-(cyclohexylamino)-6-(3-ethylureido)nicotinate iii (0.100 g, 0.320 mmol) in DMF (3 mL) at room temperature. After 15 min, m-toluidine (0.052 g, 0.480 mmol) was added and the reaction mixture stirred at room temperature for 24 h. The mixture was treated with water (5 mL) and the resulting colourless precipitate filtered, washed with water, air-dried and recrystallized from EtOH to afford Compound 3 (0.030 g, 0.076 mmol, 29%) as colourless microcrystals. 1H NMR (300 MHz, DMSO-d6): δ 10.00 (1H, s), 9.01 (1H, s), 8.44 (1H, s), 8.28 (1H, br), 8.10 (1H, d, J 9.0), 7.52 (1H, s), 7.42 (1H, d, J 9.0), 7.20 (1H, t, J 6.0), 6.90 (1H, d, J 6.0), 6.66 (1H, s), 3.25-3.13 (3H, m), 2.29 (3H, s), 1.94-1.91 (2H, m), 1.67-1.57 (3H, m), 1.42-1.23 (5H, m), 1.08 (3H, t, J 7.2); [M+H]+ m/z=396.2.

Workup

  1. filtrationthe resulting colourless precipitate filtered
  2. washwashed with water
  3. customair-dried
  4. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-e5d3ed2af351439ab6f98c16af5c2ddc
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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