Ethanol, 1-ethoxy-2,2,2-trifluoro- → HCID 18416128, compound

HRID 990967Notes

Reaction equation

HRID 990967 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[CH:26](O)[C:27]([F:30])([F:29])[F:28])C.[BH3-]C#N.[Na+]>C(O)(C(F)(F)F)=O>[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[N:19]([CH2:26][C:27]([F:30])([F:29])[F:28])[CH2:20][CH2:21][S:22][C:9]3=[CH:8][C:7]=2[N:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 9897Ethanol, 1-ethoxy-2,2,2-trifluoro-HCID 5003444Sodium cyanoborohydrideHCID 18416152HCID 18416152, compound

Product 1

HCID 18416128HCID 18416128, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

This compound was prepared according to General Method 7 (EXAMPLE 5) from 2,3-dihydro-7-isopropoxy-9-(trifluoromethyl)-1H-[1,4]thiazino[3,2-g]quinoline (11 mg, 0.034 mmol), trifluoroacetaldehyde ethyl hemiacetal (49 mg, 0.34 mmol) and NaBH3CN (14 mg, 0.22 mmol) in 0.7 mL TFA to afford 7.8 mg (56%) of 2,3-dihydro-7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]thiazino[3,2-g]quinoline, a yellow oil, after flash chromatography (9:1 hexanes:EtOAc). Data for 2,3-dihydro-7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]thiazino[3,2-g]quinoline: 1H NMR (400 MHz, CDCl3) δ 7.62 (s, 1H), 7.21 (broad s, 1H), 7.03 (s, 1H), 5.46 (hept, 1H, J=6.1), 3.97 (q, 2H, J=8.8), 3.77-3.83 (m, 2H), 3.08-3.14 (m, 2H), 1.38 (d, 6H, J=6.1).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-ae20732dfa964eb0b339e741488b86e5
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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