Diisopropylethylamine → N-(2-fluoro-5-methylphenyl)-3-[(2-{4-[(3-hydroxypyrrolidin-1-yl)carbonyl]-1H-pyrrol-2-yl}pyridin-4-yl)oxy]benzamide

HRID 521770Notes

Reaction equation

HRID 521770 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[CH:13]=[C:14]([CH:30]=[CH:31][CH:32]=1)[O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]2[NH:26][CH:25]=[C:24]([C:27](O)=[O:28])[CH:23]=2)[CH:17]=1)=[O:11].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[NH:66]1[CH2:70][CH2:69][C@H:68]([OH:71])[CH2:67]1>CN(C=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:11])[C:12]1[CH:32]=[CH:31][CH:30]=[C:14]([O:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([C:22]3[NH:26][CH:25]=[C:24]([C:27]([N:66]4[CH2:70][CH2:69][CH:68]([OH:71])[CH2:67]4)=[O:28])[CH:23]=3)[CH:17]=2)[CH:13]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733874(3S)-pyrrolidin-3-olHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 510016265-{4-[3-(2-Fluoro-5-methyl-phenylcarbamoyl)-phenoxy]-pyridin-2-yl}-1H-pyrrole-3-carboxylic acid

Product 1

HCID 67042283N-(2-fluoro-5-methylphenyl)-3-[(2-{4-[(3-hydroxypyrrolidin-1-yl)carbonyl]-1H-pyrrol-2-yl}pyridin-4-yl)oxy]benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-{4-[3-(2-Fluoro-5-methyl-phenylcarbamoyl)-phenoxy]-pyridin-2-yl}-1H-pyrrole-3-carboxylic acid (50 mg, 0.12 mmol), HATU (55 mg, 0.14 mmol) and N,N-diisopropylethylamine (34 mg, 0.26 mmol) in anhydrous DMF (8 ml) was stirred at room temperature for 10 minutes, followed by addition of (S)-3-pyrrolidinol (16 mg, 0.18 mmol). The mixture was stirred for another 10 minutes and poured into 100 ml of water. The precipitates were filtered, washed with water and dried in vacuo to give N-(2-fluoro-5-methylphenyl)-3-[(2-{4-[(3-hydroxypyrrolidin-1-yl)carbonyl]-1H-pyrrol-2-yl}pyridin-4-yl)oxy]benzamide as white solid. Yield: 40 mg, 69%.

Workup

  1. stirringThe mixture was stirred for another 10 minutes
  2. filtrationThe precipitates were filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-089ecddc54ff4857923cedf318e23ec2
Source dataset
uspto-grants-2016_05
Patent number
US09328103B2

Reaction notes

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