Diisopropylethylamine → HCID 60858052, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([OH:10])=O)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.O.ON1C2C=CC=CC=2N=N1.[F:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[CH2:35][CH2:36][NH2:37]>ClCCl>[F:31][C:32]1[CH:33]=[C:34]([CH2:35][CH2:36][NH:37][C:8]([C:5]2[N:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:10])[CH:38]=[CH:39][CH:40]=1Participants
Procedure
To a solution of 6-chloropyridazine-3-carboxylic acid (0.31 g, 1.94 mmol) in dichloromethane (15.5 mL) was added diisopropylethylamine (0.73 mL, 4.19 mmol), followed by 1-hydroxybenzotriazole monohydrate (0.28 g, 2.1 mmol) and 1-(3-dimethylamino)propyl-3-ethylcarbodiimide (0.37 mL, 2.1 mmol). The resulting mixture was stirred for 15 minutes, followed by the addition of 3-fluorophenethylamine (0.28 mL, 2.1 mmol). After stirring for 27 hours at ambient temperature, the reaction mixture was diluted with dichloromethane (200 mL), washed with water (4×25 mL), dried over Na2SO4 and concentrated in vacuo. Purification by column chromatography eluted with dichloromethane: ethyl acetate (2:1) afforded the product as a white powder (0.205 g). 1H NMR (400 MHz, CDCl3) δ 8.26, 8.12, 7.67, 7.28-7.23, 6.95-6.89, 3.80-3.75, 2.95.
Workup
- stirringAfter stirring for 27 hours at ambient temperature
- washwashed with water (4×25 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customPurification by column chromatography
- washeluted with dichloromethane: ethyl acetate (2:1)
Sources & evidence
- ORD record
- ord-8443bcf9f6f6445da43b892486ba4534
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07964591B2
Reaction notes
Loading…