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

HRID 1790670Notes

Reaction equation

HRID 1790670 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)pheylamino)-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-4deca450243547aba33d3679d2121b53
Source dataset
uspto-grants-2006_07
Patent number
US07071216B2

Reaction notes

Loading…