Acetaldehyde → HCID 54691307, compound

HRID 1244113Notes

Reaction equation

HRID 1244113 reaction equation
O[C:2]([C:4](F)(F)F)=O.[Cl:8][C:9]1[S:21][C:12]2[NH:13][C:14](=[O:20])[C:15]([C:18]#[N:19])=[C:16]([OH:17])[C:11]=2[C:10]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2([OH:36])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:24][CH:23]=1.C(=O)C.CS(C)=O.CO>CC(O)=O>[Cl:8][C:9]1[S:21][C:12]2[NH:13][C:14](=[O:20])[C:15]([C:18]#[N:19])=[C:16]([OH:17])[C:11]=2[C:10]=1[C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][C:30]2([OH:36])[CH2:35][CH2:34][N:33]([CH2:2][CH3:4])[CH2:32][CH2:31]2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 22036561Dimethyl sulfoxide methanolHCID 86596544HCID 86596544, compound

Product 1

HCID 54691307HCID 54691307, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-chloro-4-hydroxy-3-{4-[(4-hydroxypiperidin-4-yl)methoxy]phenyl}-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile TFA salt (40 mg, 0.073 mmol), acetaldehyde (0.006 mL, 0.110 mmol), and MS-CNBH3 (88 mg, 0.110 mmol, 1.25 mmol/g loading) in a 1:1 mixture of DMSO/MeOH (1 mL) containing 2% v/v AcOH was shaken in a 1 dram vial at rt for 18 h. The mixture was then filtered and purified by RP-HPLC to give the title compound. MS (ESI) m/e 460 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.24 (t, J=7.29 Hz, 3H), 1.83 (m, 2H), 1.98 (m, 2H), 3.15 (m, 4H), 3.32 (d, J=7.29 Hz, 2H), 3.87 (s, 2H), 5.22 (s, 1H), 6.92 (d, J=8.82 Hz, 2H), 7.20 (d, J=8.82 Hz, 2H), 8.91 (s, 1H), 10.77 (s, 1H).

Workup

  1. filtrationThe mixture was then filtered
  2. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-4df5670b9c0041a0a16592bacf8be530
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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