Carbodiimide → 2-Hydroxy-1-[4-(4-piperidin-4-yl-quinazolin-7-yl)-piperazin-1-yl]-ethanone

HRID 1170245Notes

Reaction equation

HRID 1170245 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([N:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)=[CH:21][CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C([O:34][CH2:35][C:36](O)=[O:37])(C)(C)C.N=C=N>C(Cl)Cl>[OH:37][CH2:36][C:35]([N:27]1[CH2:28][CH2:29][N:24]([C:20]2[CH:19]=[C:18]3[C:23]([C:14]([CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[N:15][CH:16]=[N:17]3)=[CH:22][CH:21]=2)[CH2:25][CH2:26]1)=[O:34]

Participants

5

Reactant 3

HCID 160435CarbodiimideHCID 27609982-(Tert-butoxy)acetic acidHCID 595516924-(7-Piperazin-1-yl-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 595516742-Hydroxy-1-[4-(4-piperidin-4-yl-quinazolin-7-yl)-piperazin-1-yl]-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(7-Piperazin-1-yl-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.1 mmol), prepared as described in Example 45, was added to a mixture of t-butoxyacetic acid (0.15 mmol) and PS-carbodiimide (0.2 mmol) in anhydrous DCM (2 mL). The mixture was shaken at rt overnight. It was then filtered and the resin washed with DCM. The combined filtrate and washings were concentrated in vacuo. To this was then added 3M HCl/MeOH (2 mL) and stirred at rt for 2 h and then concentrated in vacuo.

Workup

  1. filtrationIt was then filtered
  2. washthe resin washed with DCM
  3. concentrationThe combined filtrate and washings were concentrated in vacuo
  4. additionTo this was then added 3M HCl/MeOH (2 mL)
  5. stirringstirred at rt for 2 h
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a71b7cf359c84682abfdf6d83ddb60ab
Source dataset
uspto-grants-2010_11
Patent number
US07825244B2

Reaction notes

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