2-{4-[3-cyclopentyl-4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-3-hydroxybut-1-ynyl]-2-fluorophenyl)-2-methylpropanenitrile → HCID 60125006, compound

HRID 1453151Notes

Reaction equation

HRID 1453151 reaction equation
[CH:1]1([C:6]([OH:32])([CH2:22][C:23]2[O:24]C(C)(C)[O:26][C:27](=O)[CH:28]=2)[C:7]#[C:8][C:9]2[CH:14]=[C:13]([F:15])[C:12]([C:16]3([C:19]#[N:20])[CH2:18][CH2:17]3)=[C:11]([F:21])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C(O)(CC2OC(C)(C)OC(=O)C=2)C#CC2C=CC(C(C)(C)C#N)=C(F)C=2)CCCC1>>[CH:1]1([C:6]2([CH2:7][CH2:8][C:9]3[CH:14]=[C:13]([F:15])[C:12]([C:16]4([C:19]#[N:20])[CH2:18][CH2:17]4)=[C:11]([F:21])[CH:10]=3)[CH2:22][C:23](=[O:24])[CH2:28][C:27](=[O:26])[O:32]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 587626542-{4-[3-cyclopentyl-4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-3-hydroxybut-1-ynyl]-2-fluorophenyl)-2-methylpropanenitrileHCID 60125014HCID 60125014, compound

Product 1

HCID 60125006HCID 60125006, compound

Procedure

The desired product was prepared analogously to step of example A (97), substituting 1-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2,6-difluorophenyl}-cyclopropanecarbonitrile (1.0 g, 2.66 mmol) from Step 2 below in place of 2-{4-[3-cyclopentyl-4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-3-hydroxybut-1-ynyl]-2-fluorophenyl}-2-methylpropanenitrile. Yield: 0.43 g, 42%. δ: 1H NMR (CDCl3) δ: 1.35 (t, J=2.8 Hz, 2H), 1.56-1.73 (m, 10H), 1.92 (t, J=4.45 Hz, 2H), 2.21-2.30 (m, 1H), 2.65-2.79 (m, 4H), 3.44 (d, J=5.6 Hz, 2H), 6.71(d, J=8.6 Hz, 2H). MS (ESI): 386 (M−1).

Sources & evidence

ORD record
ord-56244ea56cf6422c8874c14a32e042c8
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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