tert-butyl N-(6-aminoisoquinolin-1-yl)-N-[(tert-butoxy)carbonyl]carbamate → di-tert-butyl (6-{[(4-(2-bromophenyl)-1-trityl-1H-imidazol-2-yl)(3-ethoxy-5-ethyl-2-fluorophenyl)methyl]amino}isoquinolin-1-yl)imidodicarbonate

HRID 2105027Notes

Reaction equation

HRID 2105027 reaction equation
BrC1N=C(C([NH:38][C:39]2[CH:40]=[C:41]3[C:46](=[CH:47][CH:48]=2)[C:45]([N:49]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])=[N:44][CH:43]=[CH:42]3)C2C=C(CC)C=C(OC)C=2F)N(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=1.[Br:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][C:66]=1[C:71]1[N:72]=[C:73]([CH:95]([C:97]2[CH:102]=[C:101]([CH2:103][CH3:104])[CH:100]=[C:99]([O:105][CH2:106][CH3:107])[C:98]=2[F:108])O)[N:74]([C:76]([C:89]2[CH:94]=[CH:93][CH:92]=[CH:91][CH:90]=2)([C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)[C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)[CH:75]=1.BrC1N=C(C(Cl)C2C=C(CC)C=C(OC)C=2F)N(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=1.NC1C=C2C(=CC=1)C(N(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=NC=C2>>[Br:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][C:66]=1[C:71]1[N:72]=[C:73]([CH:95]([NH:38][C:39]2[CH:40]=[C:41]3[C:46](=[CH:47][CH:48]=2)[C:45]([N:49]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C:57]([O:59][C:60]([CH3:61])([CH3:62])[CH3:63])=[O:58])=[N:44][CH:43]=[CH:42]3)[C:97]2[CH:102]=[C:101]([CH2:103][CH3:104])[CH:100]=[C:99]([O:105][CH2:106][CH3:107])[C:98]=2[F:108])[N:74]([C:76]([C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)([C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)[C:89]2[CH:90]=[CH:91][CH:92]=[CH:93][CH:94]=2)[CH:75]=1

Participants

5

Reactant 4

HCID 58717298tert-butyl N-(6-aminoisoquinolin-1-yl)-N-[(tert-butoxy)carbonyl]carbamateHCID 68812961(4-(2-bromophenyl)-1-trityl-1H-imidazol-2-yl)(3-ethoxy-5-ethyl-2-fluorophenyl)methanolHCID 688168844-bromo-2-(chloro(5-ethyl-2-fluoro-3-methoxyphenyl)methyl)-1-trityl-1H-imidazoleHCID 86607941di-tert-butyl (6-{[(4-bromo-1-trityl-1H-imidazol-2-yl)(5-ethyl-2-fluoro-3-methoxyphenyl)methyl]amino}isoquinolin-1-yl)imidodicarbonate

Product 1

HCID 86607943di-tert-butyl (6-{[(4-(2-bromophenyl)-1-trityl-1H-imidazol-2-yl)(3-ethoxy-5-ethyl-2-fluorophenyl)methyl]amino}isoquinolin-1-yl)imidodicarbonate

Procedure

According to the procedure for the preparation of Intermediate 206.4, Intermediate 217.3 (424 mg, 0.641 mmol) was converted to the chloro intermediate, then displaced with di-tert-butyl (6-aminoisoquinolin-1-yl)imidodicarbonate to afford after flash chromatography (0 to 60% EtOAc/hexanes gradient) 615 mg of intermediate 217.4 as a pale yellow solid.

Sources & evidence

ORD record
ord-aab145f98ea04cbaa9918bb09ab3bd66
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

Loading…