Sodium borohydride → HCID 86586506, compound

HRID 1350140Notes

Reaction equation

HRID 1350140 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].[BH4-].[Na+]>FC(F)(F)C(O)=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]([CH2:13][C:15]([F:18])([F:17])[F:16])[C@H:21]([CH3:23])[CH2:20][O:19][C:11]3=2)[N:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69316792HCID 69316792, compound

Product 1

HCID 86586506HCID 86586506, compoundYield 195.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

This compound was prepared according to General Method 6 (EXAMPLE 3) from (3R)-3 ,4-dihydro-8-isopropoxy-3-methyl-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline (4 mg, 0.01 mmol) and NaBH4 pellets (large excess, >10 equiv) in 2.5 mL trifluoroacetic acid (0.005 M) stirred at rt for 12 h, to afford 4 mg (80%) of (R)-3,4-dihydro-8-isopropoxy-3-methyl-4-(2,2,2-trifluoroethyl)-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline. This material (4 mg, 0.01 mmol) was carried on according to General Method 4 (EXAMPLE 1) by treatment with 2 mL acetic acid and 2 mL concentrated HCl (0.003 M) and heated at 90° C. for 4 h to afford 3.2 mg (71%) of Compound 104, after purification by column chromatography (3:1 hexanes: EtOAc to 1:1 hexanes:EtOAc, gradient elution). 1H NMR (500 MHz, CDCl3) δ 12.00 (bs, 1H), 7.16 (s, 1H), 7.11 (d, J=9.3, 1H), 7.00 (d, J=8.8, 1H), 4.20 (d, J=10.7, 2.9, 1H), 4.09 (dd, J=10.7, 2.4, 1H), 3.82 (m, 2H), 3.60 (m, 1H), 1.26 (d, J=6.8, 3H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-96cd77f4680c49968f4fe5ff38a891d7
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

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