Picolinic acid → HCID 66803437, compound

HRID 341429Notes

Reaction equation

HRID 341429 reaction equation
C(N(CC)CC)C.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36]([OH:38])=O.[NH2:39][C:40]1[N:45]=[C:44]([NH:46][C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([Cl:53])[C:48]=2[F:54])[N:43]=[C:42]([C:55](=[N:57]O)[NH2:56])[N:41]=1>CN(C=O)C>[Cl:53][C:49]1[C:48]([F:54])=[C:47]([NH:46][C:44]2[N:45]=[C:40]([NH2:39])[N:41]=[C:42]([C:55]3[N:56]=[C:36]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=4)[O:38][N:57]=3)[N:43]=2)[CH:52]=[CH:51][CH:50]=1

Participants

7

Reactant 5

HCID 1018Picolinic acidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136377136HCID 136377136, compound

Product 1

HCID 66803437HCID 66803437, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (1.10 mL, 7.58 mmol) and 1H-benzotriazol-1-ol (0.77 g, 5.05 mmol) were added to a solution of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.97 g, 5.05 mmol) in DMF (10 mL) and the mixture was stirred for 20 min at room temperature. Picolinic acid (0.62 g, 5.05 mmol) was added and the mixture was stirred for 30 min at room temperature. 4-Amino-6-[(3-chloro-2-fluorophenyl)amino]-N′-hydroxy-1,3,5-triazine-2-carboximidamide (prepared in an analogous manner to Intermediate 73, 1.50 g, 5.05 mmol) was added and the mixture was stirred at room temperature overnight before being heated to 85 C for approximately 24 h. The crude compound was purified over Ambersep resin but the impurities remained. The residue was then successively washed with EtOAc, acetone and MeOH and finally hot MeOH to afford the title compound (330 mg, 17%).

Workup

  1. stirringthe mixture was stirred for 30 min at room temperature
  2. additionwas added
  3. stirringthe mixture was stirred at room temperature overnight
  4. temperaturebefore being heated to 85 C for approximately 24 h
  5. customThe crude compound was purified over Ambersep resin
  6. washThe residue was then successively washed with EtOAc, acetone and MeOH and finally hot MeOH

Sources & evidence

ORD record
ord-f924023dc9be4756ba4aedddc1759c9b
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

Loading…