Trifluoroacetic acid → 4-(3-(8-(5,6-Dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzamido)benzoic acid

HRID 1755371Notes

Reaction equation

HRID 1755371 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:40]=[CH:41][N:42]=3)[N:15]=[C:16]([C:18]3[CH:19]=[C:20]([CH:37]=[CH:38][CH:39]=3)[C:21]([NH:23][C:24]3[CH:36]=[CH:35][C:27]([C:28]([O:30]C(C)(C)C)=[O:29])=[CH:26][CH:25]=3)=[O:22])[CH:17]=2)=[N:7][C:8]=1[O:9][CH3:10].C(O)(C(F)(F)F)=O>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:40]=[CH:41][N:42]=3)[N:15]=[C:16]([C:18]3[CH:19]=[C:20]([CH:37]=[CH:38][CH:39]=3)[C:21]([NH:23][C:24]3[CH:36]=[CH:35][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=3)=[O:22])[CH:17]=2)=[N:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71534337Tert-butyl 4-(3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzamido)benzoate

Product 1

HCID 714571424-(3-(8-(5,6-Dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzamido)benzoic acidYield 39.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-Butyl 4-(3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzamido)benzoate (80 mg, 0.14 mmol) and TFA (3 mL) in dichloromethane (3 mL) was stirred for 2 h at room temperature. The mixture was concentrated and then triturated with MeOH (2 mL) to give the product 4-(3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzamido)benzoic acid (28 mg, 39%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 10.71 (s, 1H), 10.02 (s, 1H), 8.66 (s, 1H), 8.55 (s, 1H), 8.29 (s, 1H), 8.24 (d, 1H, J=7.8 Hz), 8.12 (d, 1H, J=7.5 Hz), 7.97-7.93 (m, 2H), 7.76-7.71 (m, 3H), 7.44 (d, 1H, J=8.1 Hz), 7.13 (d, 1H, J=8.4 Hz), 4.05 (s, 3H), 3.88 (s, 3H). LC-MS: [M+H]+, 510.9, tR=1.505 min, HPLC: 97.21% at 214 nm, 99.12% at 254 nm, tR=6.006 min.

Workup

  1. concentrationThe mixture was concentrated
  2. customtriturated with MeOH (2 mL)

Sources & evidence

ORD record
ord-3c2c5c73b18640a9bda81daf2bd16c32
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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