Propanal → HCID 69319573, compound

HRID 1350141Notes

Reaction equation

HRID 1350141 reaction equation
[CH:1]([O:4][C:5]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]3[NH:22][C@H:21]([CH3:23])[CH2:20][O:19][C:11]3=2)[N:6]=1)([CH3:3])[CH3:2].[CH:24](=O)[CH2:25][CH3:26].[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[C:7](=[CH:8][CH:9]=[C:10]3[N:22]([CH2:24][CH2:25][CH3:26])[C@H:21]([CH3:23])[CH2:20][O:19][C:11]3=2)[N:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 69316792HCID 69316792, compound

Product 1

HCID 69319573HCID 69319573, compoundYield 108.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

This compound was prepared according General Method 6 (EXAMPLE 3) from (3R)-3,4-dihydro-8-isopropoxy-3-methyl-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline (11 mg, 0.03 mmol), propionaldehyde (0.3 mmol, 10 eq) and NaCNBH3 (10 equiv) in 4 mL TFA (0.03 M) stirred at rt for 12 h to afford 12 mg (100%) of (R)-3,4-dihydro-8-isopropoxy-3-methyl-4-propyl-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline. This material (12 mg, 0.030 mmol) was carried on according to General Method 4 (EXAMPLE 1) by treatment with 3 mL acetic acid and 3 mL concentrated HCl and heated at 90° C. for 4 h to afford 8 mg (75%) of Compound 105 after purification by silica gel chromatography (3:1 hexanes:EtOAc to 1:1 hexanes:EtOAc, gradient elution). 1H NMR (500 MHz, CDCl3) δ11.15 (bs, 1H), 7.10 (s, 1H), 6.99 (d, J=8.8, 1H), 6.88 (d, J=8.8, 1H), 4.11 (dd, J=10.7, 3.2, 1H), 4.03 (dd, J=10.7, 2.4, 1H), 3.51 (m, 1H), 3.30 (m, 1H), 3.14 (m, 1H), 1.64 (m, 2H), 1.21 (d, J=6.4, 3H), 0.97 (t, J=7.3, 3H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-4c56a580585d437e9e7bc0a395562a5a
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

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