1-Methylimidazole → Tert-butyl 4-(1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)pyrrolidine-3-carboxamido)benzoate

HRID 1755404Notes

Reaction equation

HRID 1755404 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:11][C:12]2[C:13]3[N:14]([CH:26]=[CH:27][N:28]=3)[N:15]=[C:16]([N:18]3[CH2:22][CH2:21][CH:20]([C:23](O)=[O:24])[CH2:19]3)[CH:17]=2)=[N:7][C:8]=1[O:9][CH3:10].[NH2:29][C:30]1[CH:42]=[CH:41][C:33]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[CH:32][CH:31]=1.CCN=C=NCCCN(C)C.CN1C=CN=C1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:11][C:12]2[C:13]3[N:14]([CH:26]=[CH:27][N:28]=3)[N:15]=[C:16]([N:18]3[CH2:22][CH2:21][CH:20]([C:23]([NH:29][C:30]4[CH:42]=[CH:41][C:33]([C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])=[CH:32][CH:31]=4)=[O:24])[CH2:19]3)[CH:17]=2)=[N:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 13901-MethylimidazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 866827461-(8-(5,6-Dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)pyrrolidine-3-carboxylic acid

Product 1

HCID 86682747Tert-butyl 4-(1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)pyrrolidine-3-carboxamido)benzoateYield 170.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)pyrrolidine-3-carboxylic acid (80 mg, 0.21 mmol), tert-butyl 4-aminobenzoate (40 mg, 0.21 mmol), EDCI (159 mg, 0.08 mmol) and 1-methyl-1H-imidazole (68 mg, 0.8 mmol) in dichloromethane (5 mL) was stirred at room temperature for 16 h. The residue was concentrated to give crude tert-butyl 4-(1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)pyrrolidine-3-carboxamido)benzoate (200 mg, crude) as brown liquid that was used directly without purification. LC-MS: 560 [M+1]+, tR=1.510 min.

Workup

  1. concentrationThe residue was concentrated

Sources & evidence

ORD record
ord-20e50a74b0bb4f2e8ae5d92605401101
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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