1-Hydroxybenzotriazole → HCID 178520339, compound

HRID 1470319Notes

Reaction equation

HRID 1470319 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][C:9]([OH:11])=O)=[CH:6][N:5]=[C:4]([N:12]2[CH:16]=[CH:15][CH:14]=[N:13]2)[N:3]=1.[CH:17]1[CH:18]=[CH:19][C:20]2[N:25](O)N=N[C:21]=2[CH:22]=1.CCN=C=NCCCN(C)C.Cl.[Cl:39]NC1C=CC=CC=1>CN(C=O)C.O>[Cl:39][C:17]1[CH:18]=[CH:19][C:20]([NH:25][C:9](=[O:11])[CH2:8][C:7]2[C:2]([OH:1])=[N:3][C:4]([N:12]3[CH:16]=[CH:15][CH:14]=[N:13]3)=[N:5][CH:6]=2)=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 258030n-chloroanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178525222HCID 178525222, compound

Product 1

HCID 178520339HCID 178520339, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidin-5-yl)acetic acid, 12-d, (150 mg, 0.68 mmol) and HOBt (101.2 mg, 0.75 mmol) in DMF (5 ml) was added EDC.HCl (144 mg, 0.75 mmol) and DIEPA (264 mg, 2.05 mmol). The solution was stirred at room temperature for 5 mins before the addition of the chlorophenyl amine (0.75 mmol) (Sigma-Aldrich). The mixture was stirred at room temperature for 24 hours. The mixture was then diluted with water and extracted with ethyl acetate. The organic layer was concentrated under vacuum and the residue was purified by silica gel column or Prep-HPLC to give the final compound 12-1. 1H NMR (DMSO-d6, 300 MHz): δ 10.23 (s, 1H), 8.56 (d, 1H), 7.92 (s, 1H), 7.63 (d, 2H), 7.37 (d, 2H), 6.64 (s, 1H), 3.53 (s, 2H). (M+H)+=330.1.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under vacuum
  3. customthe residue was purified by silica gel column or Prep-HPLC

Sources & evidence

ORD record
ord-e19de86f8470455a86201044e41b580d
Source dataset
uspto-grants-2015_04
Patent number
US09006433B2

Reaction notes

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