HCID 69710278, compound → [1-(4-hydroxy-butyl)-2-(4-methoxy-2-oxo-2H-quinolin-1-ylmethyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester

HRID 896364Notes

Reaction equation

HRID 896364 reaction equation
C(OC(=O)NCC1C=CC2N(CCCCO)C(CN3C4C(=CC=CC=4)C(=O)N(C4CC4)C3=O)=NC=2C=1)(C)(C)C.[C:40]([O:44][C:45]([NH:47][CH2:48][C:49]1[CH:82]=[CH:81][C:52]2[N:53]([CH2:70][CH2:71][CH2:72][CH2:73][O:74]C(=O)C(C)(C)C)[C:54]([CH2:56][N:57]3[C:66]4[C:61](=[CH:62][CH:63]=[CH:64][CH:65]=4)[C:60]([O:67][CH3:68])=[CH:59][C:58]3=[O:69])=[N:55][C:51]=2[CH:50]=1)=[O:46])([CH3:43])([CH3:42])[CH3:41]>O>[C:40]([O:44][C:45](=[O:46])[NH:47][CH2:48][C:49]1[CH:82]=[CH:81][C:52]2[N:53]([CH2:70][CH2:71][CH2:72][CH2:73][OH:74])[C:54]([CH2:56][N:57]3[C:66]4[C:61](=[CH:62][CH:63]=[CH:64][CH:65]=4)[C:60]([O:67][CH3:68])=[CH:59][C:58]3=[O:69])=[N:55][C:51]=2[CH:50]=1)([CH3:43])([CH3:41])[CH3:42]

Participants

4

Reactant 2

HCID 69710278HCID 69710278, compoundHCID 69718999[2-(3-Cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(4-hydroxy-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 69717811[1-(4-hydroxy-butyl)-2-(4-methoxy-2-oxo-2H-quinolin-1-ylmethyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure for the preparation of [2-(3-cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(4-hydroxy-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester was followed starting from 2,2-dimethyl-propionic acid 4-[5-(tert-butoxycarbonylamino-methyl)-2-(4-methoxy-2-oxo-2H-quinolin-1-ylmethyl)-benzoimidazol-1-yl]-butyl ester (280 mg, 0.474 mmol). After neutralization more water was added and the resulting white precipitate collected by filtration, which was washed with water (thrice) and diethyl ether (thrice) to yield 204 mg (85%) of [1-(4-hydroxy-butyl)-2-(4-methoxy-2-oxo-2H-quinolin-1-ylmethyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester as a white solid:

Workup

  1. filtrationthe resulting white precipitate collected by filtration, which
  2. washwas washed with water (thrice) and diethyl ether (thrice)

Sources & evidence

ORD record
ord-6be9f20027724e6c942053140ea04459
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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