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

HRID 13459

Reaction equation

HRID 13459 reaction equation
[CH3:1][N:2]([CH3:30])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:14]([CH3:15])[C:13]3[CH:16]=[CH:17][C:18]([O:20][C:21]4([C:27](O)=O)[CH:26]=[CH:25][CH:24]=[CH:23][NH:22]4)=[CH:19][C:12]=3[N:11]=2)=[CH:5][CH:4]=1.[N:31]1([CH2:36][CH2:37][NH2:38])[CH2:35][CH2:34]C[CH2:32]1.CN([C:42]([O:46]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>[CH3:30][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[N:14]([CH3:15])[C:13]3[CH:16]=[CH:17][C:18]([O:20][C:21]4([CH:27]5[CH2:32][N:31]([CH2:36][CH2:37][NH:38][CH:42]=[O:46])[CH2:35][CH2:34]5)[CH:26]=[CH:25][CH:24]=[CH:23][NH:22]4)=[CH:19][C:12]=3[N:11]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866171662-{[4-(Dimethylamino)phenylamino)-1-methylbenzimidazol-5-yloxy)-pyridine-2-carboxylic acid

Product 1

HCID 1317258344-(2-{[4-(dimethylamino)phenyl]amino-1-methylbenzimidazol-5-yloxy)(2-pyridyl)]-N-(2-pyrrolidinylethyl)carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-(2-{[4-(dimethylamino)phenylamino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid (1 eq) in tetrahydrofuran was added 2-pyrrolidinylethylamine (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-{[4-(dimethylamino)phenyl]amino-1-methylbenzimidazol-5-yloxy)(2-pyridyl)]-N-(2-pyrrolidinylethyl)carboxamide. MS: MH+=498.

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-32af3ed2cdb24b0daf03f3c445a8dbdb
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Linked notes

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