Hydrochloric Acid → HCID 69710278, compound

HRID 896363Notes

Reaction equation

HRID 896363 reaction equation
C(OC(=O)NCC1C=CC2N(CCC(C)C)C(CN3C4C(=CC=CC=4)C(=O)N(C4CC4)C3=O)=NC=2C=1)(C)(C)C.[CH3:40][O:41][C:42]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[NH:45][C:44](=[O:52])[CH:43]=1.[C:53]([O:57][C:58]([NH:60][CH2:61][C:62]1[CH:83]=[CH:82][C:65]2[N:66]([CH2:71][CH2:72][CH2:73][CH2:74][O:75][C:76](=[O:81])[C:77]([CH3:80])([CH3:79])[CH3:78])[C:67]([CH2:69]Cl)=[N:68][C:64]=2[CH:63]=1)=[O:59])([CH3:56])([CH3:55])[CH3:54].Cl>>[C:53]([O:57][C:58]([NH:60][CH2:61][C:62]1[CH:83]=[CH:82][C:65]2[N:66]([CH2:71][CH2:72][CH2:73][CH2:74][O:75][C:76](=[O:81])[C:77]([CH3:80])([CH3:79])[CH3:78])[C:67]([CH2:69][N:45]3[C:46]4[C:51](=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:42]([O:41][CH3:40])=[CH:43][C:44]3=[O:52])=[N:68][C:64]=2[CH:63]=1)=[O:59])([CH3:56])([CH3:54])[CH3:55]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6001674-Methoxy-1H-quinolin-2-oneHCID 59561852HCID 59561852, compoundHCID 69718855[2-(3-cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 69710278HCID 69710278, compoundYield 67%

Procedure

The procedure for the preparation of [2-(3-cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester was followed starting from 4-methoxy-1H-quinolin-2-one (106 mg, 0.605 mmol) and 2,2-dimethyl-propionic acid 4-[5-(tert-butoxycarbonylamino-methyl)-2-chloromethyl-benzoimidazol-1-yl]-butyl ester; HCl salt (296 mg, 0.605 mmol). Purification by flash chromatography (eluent hexane-ethyl acetate 1:1, 1:2, 0:1) afforded 2,2-dimethyl-propionic acid 4-[5-(tert-butoxycarbonylamino-methyl)-2-(4-methoxy-2-oxo-2H-quinolin-1-ylmethyl)-benzoimidazol-1-yl]-butyl ester (240 mg, 67%) as a white solid:

Workup

  1. customPurification by flash chromatography (eluent hexane-ethyl acetate 1:1, 1:2, 0:1)

Sources & evidence

ORD record
ord-9458f7774ef34f399396fae305910299
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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