HCID 57842775, compound → 2-(4-(2-(3-(Aminomethyl)phenylcarbamoyloxy)ethyl)-3-methylphenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acid

HRID 735580Notes

Reaction equation

NCC1C=C(NC(=O)N(CCC2C=CC(C(NC3C=C4C(=CC=3)C(N(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=NC=C4)C(O)=O)=CC=2)C)C=CC=1S(CC)(=O)=O.[C:57]([O:61][C:62]([N:64]([C:101]([O:103][C:104]([CH3:107])([CH3:106])[CH3:105])=[O:102])[C:65]1[C:74]2[C:69](=[CH:70][C:71]([NH:75][CH:76]([C:80]3[CH:85]=[CH:84][C:83]([CH2:86][CH2:87][O:88][C:89](=[O:99])[NH:90][C:91]4[CH:96]=[CH:95][CH:94]=[C:93]([C:97]#[N:98])[CH:92]=4)=[C:82]([CH3:100])[CH:81]=3)[C:77]([OH:79])=[O:78])=[CH:72][CH:73]=2)[CH:68]=[CH:67][N:66]=1)=[O:63])([CH3:60])([CH3:59])[CH3:58]>>[NH2:98][CH2:97][C:93]1[CH:92]=[C:91]([NH:90][C:89]([O:88][CH2:87][CH2:86][C:83]2[CH:84]=[CH:85][C:80]([CH:76]([NH:75][C:71]3[CH:70]=[C:69]4[C:74](=[CH:73][CH:72]=3)[C:65]([N:64]([C:62]([O:61][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:63])[C:101]([O:103][C:104]([CH3:107])([CH3:106])[CH3:105])=[O:102])=[N:66][CH:67]=[CH:68]4)[C:77]([OH:79])=[O:78])=[CH:81][C:82]=2[CH3:100])=[O:99])[CH:96]=[CH:95][CH:94]=1

Participants

Reactant 2

HCID 57842775HCID 57842775, compound

HCID 579563672-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-(3-cyanophenylcarbamoyloxy)ethyl)-3-methylphenyl)acetic acid

Product 1

HCID 579563642-(4-(2-(3-(Aminomethyl)phenylcarbamoyloxy)ethyl)-3-methylphenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acidYield 45.5%

Procedure

Using a procedure analogous to that used to prepare 25E, 30E (308 mg, 0.44 mmol) was hydrogenated for 15 h and purified by reverse phase HPLC to give 30F (140 mg, 45%) as a yellow solid. MS (ESI) m/z 700.15 (M+H)+.

Workup

custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-113bd9c06af7499a9afed8c1cf99f58c
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592331B2

Reaction notes

Loading…