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

HRID 2079671Notes

Reaction equation

HRID 2079671 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([NH:11][C:12]3[N:21]=[CH:20][C:19]4[C:14](=[CH:15][C:16]([O:22][CH:23]5[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]5)=[CH:17][CH:18]=4)[N:13]=3)=[CH:10][C:4]=2[NH:3]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH:26]1[CH2:27][CH2:28][CH:23]([O:22][C:16]2[CH:15]=[C:14]3[C:19]([CH:20]=[N:21][C:12]([NH:11][C:9]4[CH:8]=[CH:7][C:5]5[NH:6][C:2](=[O:1])[NH:3][C:4]=5[CH:10]=4)=[N:13]3)=[CH:18][CH:17]=2)[CH2:24][CH2:25]1

Participants

3

Reactant 1

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

Product 1

HCID 591992475-(7-(piperidin-4-yloxy)-quinazolin-2-ylamino]-1H-benzo[d]imidazol-2(3H)-oneYield 30%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of crude tert-butyl 4-(2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-ylamino) quinazolin-7-yloxy)piperidine-1-carboxylate in 30% TFA/DCM was stirred at room temperature for 30 min. The solvent was evaporated and crude was purified by semi-prep HPLC to provide pure product in 30% yield ES/MS m/z 377.1 (MH+).

Workup

  1. customThe solvent was evaporated
  2. customcrude was purified by semi-prep HPLC
  3. customto provide pure product in 30% yield ES/MS m/z 377.1 (MH+)

Sources & evidence

ORD record
ord-5609a8a430d94462b61a1943bcb8b3ff
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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