m-Toluidine → HCID 89651133, compound

HRID 2174222Notes

Reaction equation

HRID 2174222 reaction equation
Cl.[CH2:2](N=C=NCCCN(C)C)C.O.O[N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2N=N1.[NH2:24][C:25]1[CH:33]=[C:32](Cl)[C:28]([C:29]([OH:31])=O)=[CH:27][N:26]=1.[NH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([CH3:42])[CH:37]=1>CN(C=O)C>[NH2:24][C:25]1[N:26]=[CH:27][C:28]([C:29]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([CH3:42])[CH:37]=2)=[O:31])=[C:32]([NH:15][C:19]2[CH:18]=[CH:23][CH:22]=[C:21]([CH3:2])[CH:20]=2)[CH:33]=1

Participants

6

Reactant 4

HCID 7934m-ToluidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 72212218HCID 72212218, compound

Product 1

HCID 89651133HCID 89651133, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride and 1-hydroxybenzotriazole monohydrate were added to a stirred solution of compound iv in DMF (3 mL) at room temperature. After 15 min, the m-toluidine was added and the reaction mixture stirred at the specified temperature for 24 h. The mixture was cooled to room temperature, poured onto water and extracted with EtOAc (3×30 mL). The combined organic phase was washed with water (20 mL), saturated aqueous sodium bicarbonate (20 mL) and brine (2×20 mL), dried (MgSO4), and reduced in vacuo to give the v as a crude brown gum, which was used in the next step without further purification.

Workup

  1. additionpoured onto water
  2. extractionextracted with EtOAc (3×30 mL)
  3. washThe combined organic phase was washed with water (20 mL), saturated aqueous sodium bicarbonate (20 mL) and brine (2×20 mL)
  4. dry with materialdried (MgSO4)
  5. customto give the v as a crude brown gum, which
  6. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-b52868815b3a41a5aae8a07db3da6187
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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