Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 66669935, compound

HRID 1517900Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23](N)=[CH:22][C:21]=3[F:27])=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36]([C:38]2([C:41]([OH:43])=O)[CH2:40][CH2:39]2)=[O:37])=[CH:31][CH:30]=1.C[N:45](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([N:35]([C:32]4[CH:31]=[CH:30][C:29]([F:28])=[CH:34][CH:33]=4)[C:36]([C:38]4([C:41]([NH2:45])=[O:43])[CH2:39][CH2:40]4)=[O:37])=[CH:22][C:21]=3[F:27])=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 4-(7-(benzyloxy)quinolin-4-yloxy)-3-fluorobenzenamine) (3.6 g, 10 mmol) and 1-(4-fluorophenylcarbamoyl)cyclopropanecarboxylic acid (2.678 g, 12 mmol) in DCM (50 mL) was added TEA (1 g, 10 mmol) and HATU (6.84 g, 18 mmol) at rt. The reaction was then heated to 40° C. and stirred overnight. The mixture was washed with H2O (25 mL), and the organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (1:1 EtOAc/petroleum ether) to afford the title compound as a yellow solid (5.5 g, 97%).

Workup

washThe mixture was washed with H2O (25 mL)
dry with materialthe organic layer was dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (1:1 EtOAc/petroleum ether)

Sources & evidence

ORD record: ord-36480428a50649d383a8ef8c760f3b29
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232294B2

Reaction notes

Loading…