HCID 10254044, compound → HCID 10347289, compound

HRID 1793751Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:10]([OH:49])[CH2:11][NH:12][C:13]2[CH2:17][N:16](S(C(F)(F)F)(=O)=O)[C:15](=[O:25])[C:14]=2[C:26]2[N:30](C(OC(C)(C)C)=O)[C:29]3[CH:38]=[C:39]([N:43]4[CH2:48][CH2:47][O:46][CH2:45][CH2:44]4)[CH:40]=[C:41]([CH3:42])[C:28]=3[N:27]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].ClC1C=C([C@H](O)CNC2CNC(=O)C=2C2NC3C=C(N4CCOCC4)C=C(C)C=3N=2)C=CC=1>>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]([OH:49])[CH2:11][NH:12][C:13]2[CH2:17][NH:16][C:15](=[O:25])[C:14]=2[C:26]2[NH:30][C:29]3[CH:38]=[C:39]([N:43]4[CH2:44][CH2:45][O:46][CH2:47][CH2:48]4)[CH:40]=[C:41]([CH3:42])[C:28]=3[N:27]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

Reactant 2

HCID 10254044HCID 10254044, compound

HCID 22021547HCID 22021547, compound

Product 1

HCID 10347289HCID 10347289, compoundYield 54.5%

Procedure

4-[2-(3-Bromo-4-methoxy-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 (0.018 g, 0.023 mmol) was reacted according to the procedure used to synthesize (S)-4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-3-(4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-1,5-dihydro-pyrrol-2-one and afforded the title material (0.0068 g, 54%) as a beige solid. HPLC: 98% (220 nm), LCMS (+ESI, M+H+) m/z 542, 544, HRMS calcd for C25H28N5O4Br=541.1325, found: 541.1331; 1H NMR (400 MHz, methanol-d4) δ (ppm): 2.48 (3H, s), 3.11 (4H, br dd), 3.49 (1H, dd, J=13.8 and 6.7 Hz), 3.57 (1H, dd, J=13.8 and 4.3 Hz), 3.84–3.87 (7H, m), 4.13 (2H, 2d, J=18.0 Hz), 4.85–4.94 (1H, m), 6.75 (1H, s), 6.92 (1H, s), 6.99 (1H, d, J=8.6 Hz), 7.37 (1H, dd, J=8.6 and 2.0 Hz), 7.64 (1H, d, J=2.0 Hz).

Sources & evidence

ORD record: ord-70e0ffd8e5a940b28702b704dfc02679
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07081454B2

Reaction notes

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