Acetic Acid → HCID 66747561, compound

HRID 1019892Notes

Reaction equation

HRID 1019892 reaction equation
C=O.[CH3:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([N:9]=[CH:10][C:11]([O:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH:21]([NH:24][CH2:25][C:26]4[CH:27]=[CH:28][C:29]5[S:34][CH2:33][C:32](=[O:35])[NH:31][C:30]=5[CH:36]=4)[CH2:20][CH2:19]3)=[N:12]2)=[CH:7][CH:6]=1.[C:37](O)(=O)C.C([BH3-])#N.[Na+]>ClCCCl.CO>[CH3:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([N:9]=[CH:10][C:11]([O:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH:21]([N:24]([CH2:25][C:26]4[CH:27]=[CH:28][C:29]5[S:34][CH2:33][C:32](=[O:35])[NH:31][C:30]=5[CH:36]=4)[CH3:37])[CH2:20][CH2:19]3)=[N:12]2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66746712HCID 66746712, compound

Product 1

HCID 66747561HCID 66747561, compoundYield 22.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

Paraformaldehyde (29 mg, 0.10 mmol, 1.0 eq) is added at room temperature to a stirred solution of 6-({1-[2-(7-methoxy-quinoxalin-2-yloxy)-ethyl]-piperidin-4-ylamino}-methyl)-4H-benzo[1,4]thiazin-3-one (50 mg, 0.10 mmol, 1.0 eq) in 1,2-dichloroethane (2 mL) and methanol (0.5 mL), followed by acetic acid (7 μL, 0.12 mmol, 1.3 eq) and sodium cyanoborohydride (9 mg, 0.12 mmol, 1.3 eq). After 15 hours stirring at room temperature, the reaction mixture is extracted with dichloromethane (3×5 mL) and a saturated sodium hydrogen carbonate aqueous solution (5 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by preparative HPLC to afford 6-[({1-[2-(7-methoxy-quinoxalin-2-yloxy)-ethyl]-piperidin-4-yl}-methyl-amino)-methyl]-4H-benzo[1,4]thiazin-3-one as a light brown viscous oil (11 mg, 21% yield).

Workup

  1. extractionthe reaction mixture is extracted with dichloromethane (3×5 mL)
  2. dry with materialThe combined organic layers are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a residue that
  6. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-6236eece007244ca850c48659217dab4
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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