Hydrochloric Acid → HCID 67042591, compound

HRID 1402552Notes

Reaction equation

HRID 1402552 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:33]=[CH:32][C:16]([O:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]3[NH:28][CH:27]=[C:26]([C:29](O)=[O:30])[CH:25]=3)[CH:19]=2)=[CH:15][CH:14]=1)=[O:11].CN(C(ON1N=NC2C=[CH:46][CH:47]=[N:48][C:43]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.N1CCC1.Cl>CN(C=O)C.O>[N:48]1([C:29]([C:26]2[CH:25]=[C:24]([C:20]3[CH:19]=[C:18]([O:17][C:16]4[CH:32]=[CH:33][C:13]([NH:12][C:10]([NH:9][C:3]5[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=5[F:1])=[O:11])=[CH:14][CH:15]=4)[CH:23]=[CH:22][N:21]=3)[NH:28][CH:27]=2)=[O:30])[CH2:47][CH2:46][CH2:43]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 510012875-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrole-3-carboxylic acid

Product 1

HCID 67042591HCID 67042591, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrole-3-carboxylic acid (100 mg, 0.22 mmol), HATU (99 mg, 0.26 mmol) and N,N-diisopropylethylamine (62 mg, 0.48 mmol) in anhydrous DMF (10 ml) was stirred at room temperature for 10 minutes, followed by addition of azetidine (20 mg, 0.35 mmol). The mixture was stirred for another 5 minutes and poured into 100 ml of water. 2M HCl was added dropwise until pH=4˜5. The precipitates were filtered, washed with water and dried in vacuo to give 1-[4-({2-[4-(azetidin-1-ylcarbonyl)-1H-pyrrol-2-yl]pyridin-4-yl}oxy)phenyl]-3-(2-fluoro-5-methylphenyl)urea as light brown solid. Yield: 95 mg, 87%.

Workup

  1. stirringThe mixture was stirred for another 5 minutes
  2. filtrationThe precipitates were filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-47e6d3f9fe8a49c08a05c769045cd82c
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

Loading…