HCID 69718290, compound → HCID 69719778, compound

HRID 896361Notes

Reaction equation

C(OC(=O)NCC1C=CC2N(CCCC[F:36])C(CN3C4C(=CC=CC=4)C(=O)N(C4CC4)C3=O)=NC=2C=1)(C)(C)C.[C:40]([O:44][C:45](=[O:80])[NH:46][CH2:47][C:48]1[CH:79]=[CH:78][C:51]2[N:52]([CH2:73][CH2:74][CH2:75][CH2:76]O)[C:53]([CH2:55][N:56]3[C:65]4[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=4)[C:59](=[O:66])[N:58]([CH2:67][C:68]([F:71])([F:70])[F:69])[C:57]3=[O:72])=[N:54][C:50]=2[CH:49]=1)([CH3:43])([CH3:42])[CH3:41]>>[C:40]([O:44][C:45](=[O:80])[NH:46][CH2:47][C:48]1[CH:79]=[CH:78][C:51]2[N:52]([CH2:73][CH2:74][CH2:75][CH2:76][F:36])[C:53]([CH2:55][N:56]3[C:65]4[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=4)[C:59](=[O:66])[N:58]([CH2:67][C:68]([F:70])([F:71])[F:69])[C:57]3=[O:72])=[N:54][C:50]=2[CH:49]=1)([CH3:43])([CH3:41])[CH3:42]

Participants

Reactant 2

HCID 69718290HCID 69718290, compound

HCID 69719649HCID 69719649, compound

Product 1

HCID 69719778HCID 69719778, compoundYield 76%

Procedure

The procedure used to prepare [2-(3-cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(4-fluoro-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester was followed starting from [2-[2,4-dioxo-3-(2,2,2-trifluoro-ethyl)-3,4-dihydro-2H-quinazolin-1-ylmethyl]-1-(4-hydroxy-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester (67 mg, 0.12 mmol). Purification by flash chromatography (eluent 2%, 4% methanol in DCM) afforded [2-[2,4-dioxo-3-(2,2,2-trifluoro-ethyl)-3,4-dihydro-2H-quinazolin-1-ylmethyl]-1-(4-fluoro-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester (51 mg, 76%) as a white solid:

Workup

customPurification by flash chromatography (eluent 2%, 4% methanol in DCM)

Sources & evidence

ORD record: ord-66e094a1e276415ba99218dcc2ecf717
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919331B2

Reaction notes

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