Triethylamine → HCID 178476956, compound

HRID 1525323Notes

Reaction equation

HRID 1525323 reaction equation
[OH:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[N:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:3]=1.[NH2:17][C:18]([C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([P:33](=[O:40])([O:37][CH2:38][CH3:39])[O:34][CH2:35][CH3:36])=[CH:29][CH:28]=2)=[N:25][CH:26]=1)([CH3:20])[CH3:19].CCN(CC)CC>O=S(Cl)Cl.C(Cl)Cl>[OH:1][C:2]1[C:7]([C:8]([NH:17][C:18]([C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][C:30]([P:33](=[O:40])([O:37][CH2:38][CH3:39])[O:34][CH2:35][CH3:36])=[CH:29][CH:28]=3)=[N:25][CH:26]=2)([CH3:19])[CH3:20])=[O:10])=[CH:6][N:5]=[C:4]([C:11]2[N:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 89462508Diethyl 4-(5-(2-aminopropan-2-yl)pyridin-2-yl)phenylphosphonate2×HCID 178524753HCID 178524753, compound

Product 1

HCID 178476956HCID 178476956, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

4-hydroxy-2-(pyridazin-3-yl)pyrimidine-5-carboxylic acid, 30-ie, (200 mg, 0.92 mmol) was dissolved in SOCl2 (5 ml). The mixture was stirred at 60° C. for 4 hours, then concentrated under vacuo. The residue was dissolved with 5 ml of DCM, and added dropwise to a solution of diethyl 4-(5-(2-aminopropan-2-yl)pyridin-2-yl)phenylphosphonate, 33-g, (353 mg, 0.92 mmol) and Et3N (371 mg, 3.7 mmol) in DCM (10 ml) at 0° C. The mixture was stirred at room temperature for 5 hours and then washed with brine, dried, and concentrated under vacuo to give diethyl 4-(5-(2-(4-hydroxy-2-(pyridazin-3-yl)pyrimidine-5-carboxamido) propan-2-yl)pyridin-2-yl)phenylphosphonate (220 mg, 44%).

Workup

  1. concentrationconcentrated under vacuo
  2. dissolutionThe residue was dissolved with 5 ml of DCM
  3. stirringThe mixture was stirred at room temperature for 5 hours
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-4a5df97a854843679cef21112f1e54f4
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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