HCID 58666633, compound → HCID 22021459, compound

HRID 1354655Notes

Reaction equation

HRID 1354655 reaction equation
[OH:1][C:2]1CNC(=O)C=1C1N(C(OC(C)(C)C)=O)C2C=C(N3CCOCC3)C=C(C)C=2N=1.[Cl:31][C:32]1[CH:33]=[C:34]([C@H:38]([OH:77])[CH2:39][NH:40][C:41]2[CH2:45][N:44]([S:46]([C:49]([F:52])([F:51])[F:50])(=[O:48])=[O:47])[C:43](=[O:53])[C:42]=2[C:54]2[N:58]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[C:57]3[CH:66]=[C:67]([N:71]4[CH2:76][CH2:75][O:74][CH2:73][CH2:72]4)[CH:68]=[C:69]([CH3:70])[C:56]=3[N:55]=2)[CH:35]=[CH:36][CH:37]=1>C(#N)C>[Cl:31][C:32]1[CH:33]=[C:34]([CH:38]([OH:77])[CH2:39][NH:40][C:41]2[CH2:45][N:44]([S:46]([C:49]([F:51])([F:50])[F:52])(=[O:47])=[O:48])[C:43](=[O:53])[C:42]=2[C:54]2[N:58]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[C:57]3[CH:66]=[C:67]([N:71]4[CH2:76][CH2:75][O:74][CH2:73][CH2:72]4)[CH:68]=[C:69]([CH3:70])[C:56]=3[N:55]=2)[CH:35]=[CH:36][C:37]=1[O:1][CH3:2]

Participants

4

Reactant 2

HCID 58666633HCID 58666633, compoundHCID 135681558HCID 135681558, compound

Product 1

HCID 22021459HCID 22021459, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Hydroxy-3-(1-tert-butyloxycarbonyl-4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-1,5-dihydro-pyrrol-2-one (0.032 g, 0.059 mmol) was reacted as described in the procedure used to synthesize (S)-4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-3-(1-tert-butyloxycarbonyl-4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-1-trifluoromethanesulfonyl-1,5-dihydro-pyrrol-2-one and by using acetonitrile instead of N,N-dimethylformamide. This gave the title material (0.018 g, 35%). LCMS (+ESI, M+H+) m/z 730; 1H NMR (400 MHz, methanol-d4) δ (ppm): 1.55 (9H, s), 2.57 (3H, s), 3.20 (4H, m), 3.40 (2H, d, J=5.9 Hz), 3.85 (7H, m), 4.31 (1H, d, J=17.5 Hz), 4.44 (1H, d, J=17.6 Hz), 4.72 (1H, t, J=5.7 Hz), 7.02–7.04 (2H, m), 7.18 (1H, s), 7.30 (1H, d, J=8.4 Hz), 7.44 (1H, s).

Sources & evidence

ORD record
ord-1add10e479114c81ad84b2392d694375
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

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