1-Pyrrolidineethanamine → 4-(2-{[2-fluro-5-(trifluromethyl)phenyl]amino-1-methylbenzimidazol-5-yloxy)-(2-pyridyl)]-N-(2-pyrrolidinylethyl)carboxamide

HRID 2070264Notes

Reaction equation

HRID 2070264 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13]1[N:17]([CH3:18])[C:16]2[CH:19]=[CH:20][C:21]([O:23][C:24]3(C(O)=O)[CH:29]=[CH:28][CH:27]=[CH:26][NH:25]3)=[CH:22][C:15]=2[N:14]=1.[N:33]1([CH2:38][CH2:39][NH2:40])[CH2:37][CH2:36][CH2:35][CH2:34]1.CN([C:44]([O:48]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13]1[N:17]([CH3:18])[C:16]2[CH:19]=[CH:20][C:21]([O:23][C:24]3([CH:36]4[CH2:37][N:33]([CH2:38][CH2:39][NH:40][CH:44]=[O:48])[CH2:34][CH2:35]4)[CH:29]=[CH:28][CH:27]=[CH:26][NH:25]3)=[CH:22][C:15]=2[N:14]=1

Participants

6

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 865921992-{[2-Fluoro-5-(trifluoromethyl)phenylamino)-1-methylbenzimidazol-5-yl-oxy)pyridine-2-carboxylic acid

Product 1

HCID 1317258364-(2-{[2-fluro-5-(trifluromethyl)phenyl]amino-1-methylbenzimidazol-5-yloxy)-(2-pyridyl)]-N-(2-pyrrolidinylethyl)carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-(2-{[2-fluoro-5-(trifluoromethyl)phenylamino)-1-methylbenzimidazol-5-yl-oxy)pyridine-2-carboxylic acid (1 eq) in tetrahydrofuran was added 2-pyrrolidinyl-ethylamine (2 eq), HBTU (2 eq) and N,N-diisopropylethylamine (4 eq) and stir at ambient temperature for 16 h. The mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was concentrated and preparative chromatography yielded [4-(2-{[2-fluoro-5-(trifluoromethyl)phenyl]amino-1-methylbenzimidazol-5-yloxy)(2-pyridyl)]-N-(2-pyrrolidinylethyl)carboxamide. MS: MH+=542.

Workup

  1. concentrationThe mixture was then concentrated
  2. custompartitioned between ethyl acetate and water
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-5653bd5ab33c44d3a2139ca27e5af1a7
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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