4-{2-[3-(3-Dimethylamino-benzoylamino)-phenyl]-oxazolo[4,5-b]pyridin-5-ylmethyl}-piperazine-1-carboxylic acid tert-butyl ester → 3-dimethylamino-N-[3-(5-piperazin-1-ylmethyl-oxazolo[4,5-b]pyridin-2-yl)-phenyl]-benzamide

HRID 419865Notes

Reaction equation

HRID 419865 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[N:20]=[C:19]3[N:21]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31](=[O:41])[C:32]5[CH:37]=[CH:36][CH:35]=[C:34]([N:38]([CH3:40])[CH3:39])[CH:33]=5)[CH:25]=4)[O:23][C:18]3=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:39][N:38]([CH3:40])[C:34]1[CH:33]=[C:32]([CH:37]=[CH:36][CH:35]=1)[C:31]([NH:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([C:22]2[O:23][C:18]3[C:19]([N:21]=2)=[N:20][C:15]([CH2:14][N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:16][CH:17]=3)[CH:25]=1)=[O:41]

Participants

4

Reactant 1

HCID 666248784-{2-[3-(3-Dimethylamino-benzoylamino)-phenyl]-oxazolo[4,5-b]pyridin-5-ylmethyl}-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 596804203-dimethylamino-N-[3-(5-piperazin-1-ylmethyl-oxazolo[4,5-b]pyridin-2-yl)-phenyl]-benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent2×

Procedure

4-{2-[3-(3-Dimethylamino-benzoylamino)-phenyl]-oxazolo[4,5-b]pyridin -5-ylmethyl}-piperazine -1-carboxylic acid tert-butyl ester (25 mg, 0.045 mmol) was dissolved in 1 mL of 25% TFA in CH2Cl2 and allowed to stand at room temperature for 1 hour. It was then concentrated and the resulting residue was triturated with Et2O to afford essentially quantitative yield of 3-dimethylamino-N-[3-(5-piperazin-1-ylmethyl-oxazolo [4,5-b]pyridin-2-yl)-phenyl]-benzamide as the TFA salt.

Workup

  1. concentrationIt was then concentrated
  2. customthe resulting residue was triturated with Et2O

Sources & evidence

ORD record
ord-e485c47617064892afe5adcae681bd9c
Source dataset
uspto-grants-2012_01
Patent number
US08093401B2

Reaction notes

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