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 68865238, compound

HRID 1453157Notes

Reaction equation

[CH:1]1([C:6]([OH:34])([CH2:24][C:25]2[O:26]C(C)(C)O[C:29](=[O:31])[CH:30]=2)[C:7]#[C:8][C:9]2[CH:14]=[C:13]([F:15])[C:12]([C:16]([CH2:21][CH3:22])([CH2:19][CH3:20])[C:17]#[N:18])=[C:11]([F:23])[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]([CH2:21][CH3:22])([CH2:19][CH3:20])[C:17]#[N:18])=[C:11]([F:23])[CH:10]=3)[CH2:24][C:25](=[O:26])[CH2:30][C:29](=[O:31])[O:34]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

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-methylpropanenitrile

HCID 68866352HCID 68866352, compound

Product 1

HCID 68865238HCID 68865238, compound

Procedure

The desired product was prepared analogously to Example A (97), step 4, substituting 2-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2,6-difluorophenyl}-2-ethyl-butyronitrile (3.11 g, 6.55 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: 1.52 g, 56%. 1H NMR (CDCl3) δ: 1.03 (t, J=3.65 Hz, 6H), 1.18-1.29 (m, 2H), 1.38-1 42 (m, 1H), 1.60-1.82 (m, 4H), 1.92-2.09 (m, 5H), 2.23-2.29 (m, 3H), 2.63-2.80 (m, 4H), 3.45 (d, J=3.6 Hz, 2H) 6.73 (d, J=10.8 Hz, 2H). MS (ESI): 416 (M−1).

Sources & evidence

ORD record: ord-1202f7c72f50457a88a4df25ae585cc4
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473790B2

Reaction notes

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