HCID 68893121, compound → HCID 68894430, compound

HRID 1821006Notes

Reaction equation

HRID 1821006 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:20][C:19]=3[CH3:33])[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[H][H]>[Pd].CO.CCOC(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])=[CH:20][C:19]=3[CH3:33])[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]

Participants

5

Reactant 2

HCID 68893121HCID 68893121, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68894430HCID 68894430, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 120 mg (0.26 mmol) of tert-butyl 3-(4-(5-(3-cyano-4-isopropyloxyphenyl)-1,2,4-thiadiazol-3-yl)-3-methylphenyl)-2-propenoate (from Step C) and 41 mg of palladium on activated carbon (10% w/w; 0.025 mmol) in 15 mL of methanol/EtOAc (1/1) was hydrogenated under atmospheric pressure of hydrogen for 2 h. The heterogeneous mixture was filtered through a disposable frit to remove palladium and the filtrate was concentrated. The crude product was found to be pure by ESI-MS and 1H NMR analyses and used in subsequent step without purification: 1H NMR (500 MHZ, CDCl3) δ 1.46 (s, 9H), 1.49 (d, J=6.5, 6H), 2.61 (t, J=7.5, 2H), 2.65 (s, 3H), 2.97 (t, J=7.5, 2H), 4.79 (sep, J=6.5, 1H), 7.11 (d, J=9.0, 1H), 7.18 (d, J=9.0, 1H), 7.23 (s, 1H), 7.69 (d, J=8.0, 1H), 8.18 (d, J=2.0, 1H), 8.24 (dd, J=8.0, 2.0, 1H).

Workup

  1. filtrationThe heterogeneous mixture was filtered through a disposable frit
  2. customto remove palladium
  3. concentrationthe filtrate was concentrated
  4. customused in subsequent step without purification

Sources & evidence

ORD record
ord-78e4aba8586040d6a2d29dc95c6a5b5b
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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