Acetic Acid → (R)-6-[[3-[[4-[2-[[2-[8-(Benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-hydroxyethyl]amino]ethyl]-phenyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

HRID 1944953Notes

Reaction equation

HRID 1944953 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:66][Si](C(C)(C)C)(C)C)[CH2:21][NH:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32]([C:34]3[CH:35]=[C:36]([S:40]([C:43]4[CH:44]=[C:45]5[C:50](=[C:51]([CH3:53])[CH:52]=4)[N:49]=[CH:48][C:47]([C:54]([NH2:56])=[O:55])=[C:46]5[NH:57][C:58]4[CH:63]=[CH:62][CH:61]=[C:60]([O:64][CH3:65])[CH:59]=4)(=[O:42])=[O:41])[CH:37]=[CH:38][CH:39]=3)=[O:33])=[CH:27][CH:26]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(O)(=O)C>C(#N)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([OH:66])[CH2:21][NH:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([NH:31][C:32]([C:34]3[CH:35]=[C:36]([S:40]([C:43]4[CH:44]=[C:45]5[C:50](=[C:51]([CH3:53])[CH:52]=4)[N:49]=[CH:48][C:47]([C:54]([NH2:56])=[O:55])=[C:46]5[NH:57][C:58]4[CH:63]=[CH:62][CH:61]=[C:60]([O:64][CH3:65])[CH:59]=4)(=[O:42])=[O:41])[CH:37]=[CH:38][CH:39]=3)=[O:33])=[CH:29][CH:30]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 86659112(R)-6-[[3-[[4-[2-[[2-[8-(Benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-[(tert-butyldimethylsilyl)oxy]ethyl]amino]ethyl]phenyl]carbamoyl]-phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

Product 1

HCID 86659111(R)-6-[[3-[[4-[2-[[2-[8-(Benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-hydroxyethyl]amino]ethyl]-phenyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Intermediate 140 (135 mg, 0.133 mmol) was combined with TBAF (1M/THF, 0.4 mL) and acetic acid (23 μL) in anhydrous acetonitrile (0.2 mL) and allowed to stir at rt. After 18 h, the reaction was concentrated in vacuo to a brown oil, which was suspended in H2O. The solid was filtered and washed with H2O and hexane, then dried to give the title compound as a yellow solid, 124 mg, which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 10.80 (s, 1H), 10.46 (s, 1H), 9.09 (s, 1H), 8.37 (s, 1H), 8.32 (s, 1H), 8.30 (br s, 1H), 8.16-8.24 (m, 2H), 8.03 (s, 1H), 7.86 (d, J=7.9 Hz, 1H), 7.77 (br s, 1H), 7.76 (dd, J=7.6, 15.6 Hz, 1H), 7.66 (d, J=8.3 Hz, 2H), 7.55 (d, J=7.6 Hz, 2H), 7.32-7.41 (m, 2H), 7.26-7.32 (m, 1H), 7.07-7.23 (m, 5H), 6.61-6.69 (m, 2H), 6.49-6.59 (m, 2H), 5.28 (s, 2H), 5.03 (t, J=6.1 Hz, 1H), 3.60 (s, 3H), 3.15-3.19 (m, 2H), 2.70 (s, 3H), 2.62-2.81 (m, 7H). ES/MS calcd. for C51H47N6O8S+ 903.3. Found m/z=903.3 (M+H+).

Workup

  1. concentrationthe reaction was concentrated in vacuo to a brown oil, which
  2. filtrationThe solid was filtered
  3. washwashed with H2O and hexane
  4. customdried

Sources & evidence

ORD record
ord-010cdff52b5b47a38c0887e1fbb54637
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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