Acetic Anhydride → HCID 54702792, compound

HRID 1244114Notes

Reaction equation

HRID 1244114 reaction equation
[OH:1][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.CCN(CC)CC.CC(OC(C)=O)=O>C(Cl)Cl>[C:2]([N:33]1[CH2:34][CH2:35][C:30]([CH2:29][O:28][C:25]2[CH:24]=[CH:23][C:22]([C:10]3[C:11]4[C:16]([OH:17])=[C:15]([C:18]#[N:19])[C:14](=[O:20])[NH:13][C:12]=4[S:21][C:9]=3[Cl:8])=[CH:27][CH:26]=2)([OH:36])[CH2:31][CH2:32]1)(=[O:1])[CH3:4]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 86596544HCID 86596544, compound

Product 1

HCID 54702792HCID 54702792, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ambient solution 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), Et3N (0.015 mL, 0.11 mmol), and Ac2O (0.007 mL, 0.073 mmol) in DCM (0.5 mL) was stirred for 18 h. The reaction was then quenched by the addition of saturated NaHCO3 (1 mL) and EtOAc (1 mL). The layers were separated, and the aqueous was extracted with additional EtOAc (2×1 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by RPLC to give the title compound. MS (ESI) m/e 474 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.61 (m, 4H), 2.01 (s, 3H), 2.94 (m, 2H), 3.4 (m, 2H), 3.81 (s, 2H), 6.95 (d, J=8.81 Hz, 2H), 7.22 (d, J=8.48 Hz, 2H).

Workup

  1. customThe reaction was then quenched by the addition of saturated NaHCO3 (1 mL) and EtOAc (1 mL)
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with additional EtOAc (2×1 mL)
  4. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by RPLC

Sources & evidence

ORD record
ord-ca909001fd6b4ee18ec1c3630522b96b
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

Loading…