5-Amino-2-hydroxybenzimidazole → tert-butyl 4-(2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-ylamino) quinazolin-7-yloxy)piperidine-1-carboxylate

HRID 2079670Notes

Reaction equation

HRID 2079670 reaction equation
C(S([C:6]1[N:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([O:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[CH:11][CH:12]=2)[N:7]=1)(=O)=O)C.[NH2:30][C:31]1[CH:40]=[CH:39][C:34]2[NH:35][C:36](=[O:38])[NH:37][C:33]=2[CH:32]=1>C(#N)C>[O:38]=[C:36]1[NH:35][C:34]2[CH:39]=[CH:40][C:31]([NH:30][C:6]3[N:15]=[CH:14][C:13]4[C:8](=[CH:9][C:10]([O:16][CH:17]5[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:19][CH2:18]5)=[CH:11][CH:12]=4)[N:7]=3)=[CH:32][C:33]=2[NH:37]1

Participants

4

Reactant 2

HCID 667655-Amino-2-hydroxybenzimidazoleHCID 67102269Tert-butyl 4-(2-(ethylsulfonyl) quinazolin-7-yloxy)piperidine-1-carboxylate

Product 1

HCID 67102611tert-butyl 4-(2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-ylamino) quinazolin-7-yloxy)piperidine-1-carboxylateYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of tert-butyl 4-(2-(ethylsulfonyl) quinazolin-7-yloxy)piperidine-1-carboxylate (1 eq) and 5-amino-1,3-dihydro-benzimidazole-2-one (5 eq) in acetonitrile was heated in sealed tube at 110° C. for 48 h. The product was filtered, washed and dried. A brown solid, yield 50%. ES/MS m/z 477.5 (MH+).

Workup

  1. filtrationThe product was filtered
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-2cdb2005d53944d4bed28df775abd90e
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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