Diisopropylethylamine → 6-Chloro-3-(2-fluoro-4-iodo-phenylamino)-pyridazine-4-carboxylic acid (2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-amide

HRID 500517Notes

Reaction equation

HRID 500517 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=2[F:16])=[C:4]([C:17]([OH:19])=O)[CH:3]=1.[CH3:20][C:21]1([CH3:29])[O:25][CH:24]([CH2:26][O:27][NH2:28])[CH2:23][O:22]1.C(N(C(C)C)CC)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl>[CH3:20][C:21]1([CH3:29])[O:25][CH:24]([CH2:26][O:27][NH:28][C:17]([C:4]2[CH:3]=[C:2]([Cl:1])[N:7]=[N:6][C:5]=2[NH:8][C:9]2[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=2[F:16])=[O:19])[CH2:23][O:22]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 10240948O-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]hydroxylamineHCID 248220276-Chloro-3-[(2-fluoro-4-iodophenyl)amino]pyridazine-4-carboxylic acid

Product 1

HCID 248220306-Chloro-3-(2-fluoro-4-iodo-phenylamino)-pyridazine-4-carboxylic acid (2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-chloro-3-(2-fluoro-4-iodo-phenylamino)-pyridazine-4-carboxylic acid (46 mg, 0.12 mmol), O-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-hydroxylamine (18.9 mg, 0.13 mmol) and diisopropyl ethylamine (27.2 mg, 0.21 mmol) in dichloromethane, was added PyBop (36.4 mg, 0.06 mmol). The reaction was carried out at room temperature for 5 hours. The mixture was concentrated and purified by flash chromatography to afford the desired adduct. LC/MS [9.50 min; 523 (M+1)].

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-742b8c755b45473ead98927fb299b556
Source dataset
uspto-grants-2010_08
Patent number
US07772233B2

Reaction notes

Loading…