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

HRID 2070260

Reaction equation

HRID 2070260 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-c37401f37b4f40d3a20d061e078eccf9
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Linked notes

Loading…