Formaldehyde → HCID 18416179, compound

HRID 990966Notes

Reaction equation

HRID 990966 reaction equation
[CH:1]([O:4][C:5]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]2[CH:11]=[C:10]3[NH:19][CH2:20][CH2:21][S:22][C:9]3=[CH:8][C:7]=2[N:6]=1)([CH3:3])[CH3:2].C=O.[BH3-][C:26]#N.[Na+]>C(O)(=O)C>[CH3:26][N:19]1[C:10]2=[CH:11][C:12]3[C:13]([C:15]([F:18])([F:17])[F:16])=[CH:14][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[N:6][C:7]=3[CH:8]=[C:9]2[S:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 18416152HCID 18416152, compound

Product 1

HCID 18416179HCID 18416179, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2,3-dihydro-7-isopropoxy-9-(trifluoromethyl)-1H-[1,4]thiazino[3,2-g]quinoline (11 mg, 0.033 mmol) and paraformaldehyde (9.9 mg, 0.33 mmol) in 0.5 mL acetic acid was added NaBH3CN (12 mg, 0.19 mmol). After 16 h, the solution was quenched with sat'd NaHCO3 (20 mL), and was extracted with EtOAc (20 mL). The organic layer was washed sequentially with sat'd NaHCO3 (10 mL) and brine (10 mL), dried over MgSO4, filtered and concentrated to afford 11 mg (97%) of 2,3-dihydro-1-methyl-7-isopropoxy-9-(trifluoromethyl)-1H-[1,4]thiazino[3,2-g]quinoline, a yellow solid. Data for 2,3-dihydro-1-methyl-7-isopropoxy-9-(trifluoromethyl)-1H-[1,4]thiazino[3,2-g]quinoline: 1H NMR (400 MHz, CDCl3) δ 7.60 (s, 1H), 7.01 (s, 1H), 6.98 (broad s, 1H), 5.45 (hept, 1H, J=6.2), 3.58-3.64 (m, 2H), 3.14-3.20 (m, 2H), 3.05 (s, 3H), 1.37 (d, 6H, j=6.2).

Workup

  1. customthe solution was quenched with sat'd NaHCO3 (20 mL)
  2. extractionwas extracted with EtOAc (20 mL)
  3. washThe organic layer was washed sequentially with sat'd NaHCO3 (10 mL) and brine (10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a8744ccf87b04ce08154f27d17a35413
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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