4-(Adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzonitrile → 4-(Adamantan-1-ylmethoxy)-3-cyclopropylbenzamide

HRID 1849503Notes

Reaction equation

HRID 1849503 reaction equation
[C:1]12([CH2:11][O:12][C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=3[C:21]3C(OC)=NC=[CH:25][CH:26]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C12(C[O:40]C3C=CC(C#N)=CC=3C3CC3)CC3CC(CC(C3)C1)C2>>[C:1]12([CH2:11][O:12][C:13]3[CH:20]=[CH:19][C:16]([C:17]([NH2:18])=[O:40])=[CH:15][C:14]=3[CH:21]3[CH2:26][CH2:25]3)[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

3

Reactant 2

HCID 867028444-(Adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzonitrileHCID 867028474-(Adamantan-1-ylmethoxy)-3-cyclopropylbenzonitrile

Product 1

HCID 867028484-(Adamantan-1-ylmethoxy)-3-cyclopropylbenzamide

Procedure

Following the procedure as described in Example 38 step 3 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzonitrile with 4-(adamantan-1-ylmethoxy)-3-cyclopropylbenzonitrile, the title compound was obtained as a colorless solid (0.48 g, 97%): 1H NMR (300 MHz, CDCl3) δ 7.57-7.53 (m, 1H), 7.37-7.35 (m, 1H), 6.81-6.76 (m, 1H), 5.69 (br s, 2H), 3.55 (s, 2H), 2.19-2.09 (m, 1H), 2.04 (br s, 3H), 1.90-1.67 (m, 12H), 0.98-0.91 (m, 2H), 0.73-0.66 (m, 2H); MS (ES+) m/z: 326.2 (M+1).

Sources & evidence

ORD record
ord-e3c23751942a4c6da955440037792566
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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