2-Piperidineethanamine → HCID 131725839, compound

HRID 13470Notes

Reaction equation

HRID 13470 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([O:22][C:23]4(C(O)=O)[CH:28]=[CH:27][CH:26]=[CH:25][NH:24]4)=[CH:21][C:14]=3[N:13]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]1[CH2:38][CH2:39][NH2:40].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>[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([O:22][C:23]4([CH:35]5[CH2:36][CH2:37][NH:32][CH:33]([CH2:38][CH2:39][NH:40][CH:44]=[O:48])[CH2:34]5)[CH:28]=[CH:27][CH:26]=[CH:25][NH:24]4)=[CH:21][C:14]=3[N:13]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 275682-PiperidineethanamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 865922052-{[3-(Tert-butyl)phenylamino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid

Product 1

HCID 131725839HCID 131725839, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-(2-{[3-(tert-butyl)phenylamino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid (1 eq) in tetrahydrofuran was added 2-piperidylethylamine (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-{[3-(tert-butyl)phenyl]amino-1-methylbenzimidazol-5-yloxy)(2-pyridyl)]-N-(2-piperidylethyl)carboxamide. MS: MH+=512.

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-b59ea792e2524b1b969fcb0889556eab
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Reaction notes

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