Acetic Acid → HCID 53936018, compound
Reaction equation
C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([SiH2][O:28][C:29](C)(C)[C@@H:30]1[N:35]([CH2:36][C:37]2[NH:45][C:44]3[CH:43]=[CH:42][N:41]=[CH:40][C:39]=3[CH:38]=2)[C:34](=[O:46])[CH2:33][N:32]([S:47]([CH:50]=[CH:51][C:52]2[S:53][C:54]([Cl:57])=[CH:55][CH:56]=2)(=[O:49])=[O:48])[CH2:31]1)(C)(C)C>C1COCC1>[Cl:57][C:54]1[S:53][C:52]([CH:51]=[CH:50][S:47]([N:32]2[CH2:31][C@H:30]([CH2:29][OH:28])[N:35]([CH2:36][C:37]3[NH:45][C:44]4[CH:43]=[CH:42][N:41]=[CH:40][C:39]=4[CH:38]=3)[C:34](=[O:46])[CH2:33]2)(=[O:48])=[O:49])=[CH:56][CH:55]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Glacial acetic acid (3 mL, 0.046 mmol) and tetrabutylammonium fluoride (92 mL, 0.092 mmol) is added to a solution of 6-(R)-(tert-butyl-dimethyl-silanyloxymethyl)-4-[2-(5-chloro-thiophen-2-yl)-ethenesulfonyl]-1-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-piperazin-2-one (0.019 g, 0.033 mmol) in THF (0.5 mL). The resulting solution is stirred for 4 h then concentrated in vacuo. The crude product is purified by RP-HPLC eluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 100% CH3CN and the appropriate product fractions are lyophilized to provide the title compound (0.009 g, 0.016 mmol) as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ14.50 (bs, 1H), 12.60 (bs, 1H), 9.18 (s, 1H), 8.38 (d, 1H), 7.89 (d, 1H), 7.61 (d, 1H), 7.50 (d, 1H), 7.21 (d, 1H), 7.08 (d, 1H), 6.90 (s, 1H), 5.03 (s, 2H), 4.63 (d, 2H), 3.70-3.90 (AB, 2H), 3.75 (m, 1H), 3.21 (m, 2H). Ion spray MS, [M+H]+467, 469, Cl pattern.
Workup
- concentrationthen concentrated in vacuo
- customThe crude product is purified by RP-HPLC
- washeluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 100% CH3CN
Sources & evidence
- ORD record
- ord-25d1f25496fb4cc49f0abda71c6f6703
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07612075B2
Reaction notes
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