Triethylamine → 6-[4-(4-Chloro-phthalazin-1-yl)-piperazin-1-yl]-nicotinic acid ethyl ester

HRID 42204

Reaction equation

HRID 42204 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[N:7][CH:6]=1)[CH3:2].[Cl:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](Cl)=[N:21][N:20]=1.C(N(CC)CC)C.CN1C(=O)CCC1>O>[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:12][CH2:13][N:14]([C:22]3[C:23]4[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:19]([Cl:18])=[N:20][N:21]=3)[CH2:15][CH2:16]2)=[N:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 784901,4-DichlorophthalazineHCID 14987933Ethyl 6-(piperazin-1-yl)nicotinate

Product 1

HCID 574716166-[4-(4-Chloro-phthalazin-1-yl)-piperazin-1-yl]-nicotinic acid ethyl esterYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 6-piperazin-1-yl-nicotinic acid ethyl ester (1.30 g, 5.40 mmol), 1,4-dichlorophthalazine (932 mg, 4.59 mmol), triethylamine (1.78 mL, 13.50 mmol), and NMP (8 mL) and heat to 85° C. for 6 h. Cool to room temperature, dilute with H2O (50 mL) and extract organics with EtOAc (3×50 mL). Combined organic layers are dried over MgSO4 and concentrated. Resulting solid is triturated with EtOAc to give the title compound as a fine tan powder (895 mg, 49% yield).

Workup

  1. extractionextract organics with EtOAc (3×50 mL)
  2. dry with materialCombined organic layers are dried over MgSO4
  3. concentrationconcentrated
  4. customResulting solid
  5. customis triturated with EtOAc

Sources & evidence

ORD record
ord-1f3c4c1675544c09b427902408c8625c
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Linked notes

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