1-Hydroxybenzotriazole → N-(6'-Amino-3''-fluoro-3,2':3',4''-terpyridin-5'-yl)pyrimidine-5-carboxamide

HRID 2264213Notes

Reaction equation

HRID 2264213 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([OH:9])=O)[CH:4]=[N:3][CH:2]=1.Cl.CN(C)CCCN=C=NCC.N1(O)C2C=CC=CC=2N=N1.[F:32][C:33]1[CH:34]=[N:35][CH:36]=[CH:37][C:38]=1[C:39]1[C:40]([C:47]2[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=2)=[N:41][C:42]([NH2:46])=[C:43]([NH2:45])[CH:44]=1>CN(C=O)C>[NH2:46][C:42]1[N:41]=[C:40]([C:47]2[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=2)[C:39]([C:38]2[CH:37]=[CH:36][N:35]=[CH:34][C:33]=2[F:32])=[CH:44][C:43]=1[NH:45][C:7]([C:5]1[CH:4]=[N:3][CH:2]=[N:1][CH:6]=1)=[O:9]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 78346Pyrimidine-5-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 595959543''-Fluoro-3,2':3',4''-terpyridine-5',6'-diamine2×

Product 1

HCID 59595970N-(6'-Amino-3''-fluoro-3,2':3',4''-terpyridin-5'-yl)pyrimidine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of pyrimidine-5-carboxylic acid (0.088 g, 0.709 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.136 g, 0.709 mmol) and 1H-1,2,3-benzotriazol-1-ol (0.072 g, 0.534 mmol) in DMF (4 mL) was heated at 40° C. for 15 minutes. Finally, 3″-fluoro-3,2′:3′,4″-terpyridine-5′,6′-diamine (Intermediate 1, 0.15 g, 0.534 mmol) in DMF (4 mL) was added and the mixture was stirred at room temperature overnight. The crude mixture was extracted between ethyl acetate and water. The organic layer was washed with 4% sodium bicarbonate aqueous solution and water, dried (MgSO4) and evaporated. The residue (0.2 g) was used in the next step without further purification.

Workup

  1. extractionThe crude mixture was extracted between ethyl acetate and water
  2. washThe organic layer was washed with 4% sodium bicarbonate aqueous solution and water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue (0.2 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-5d907f657c824eae87a8a4f32e525a6c
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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