6-(1,4-Diazepan-1-yl)nicotinonitrile → HCID 53327836, compound

HRID 874963Notes

Reaction equation

HRID 874963 reaction equation
[N:1]1([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:16][C:17]([F:33])([F:32])[C:18]1[O:22][N:21]=[C:20]([C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=2)[C:26](O)=[O:27])[N:19]=1>>[F:32][C:17]([F:16])([F:33])[C:18]1[O:22][N:21]=[C:20]([C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=2)[C:26]([N:4]2[CH2:5][CH2:6][CH2:7][N:1]([C:8]3[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=3)[CH2:2][CH2:3]2)=[O:27])[N:19]=1

Participants

3

Reactant 2

HCID 27471016-(1,4-Diazepan-1-yl)nicotinonitrileHCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid

Product 1

HCID 53327836HCID 53327836, compoundYield 34%

Procedure

This compound was synthesized from 6-(1,4-diazepan-1-yl)nicotinonitrile and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described for example 37 step 3 (80 mg, yield 34%). 1H NMR (400 MHz, MeOD) δ 8.20-8.18 (m, 1H), 8.02 (m, 1H), 7.69-7.65 (m, 1H), 7.60 (t, J=7.7 Hz, 1H), 7.55 (m, 1H), 7.38 (d, J=7.8 Hz, 1H), 6.78-6.76 (m, 1H), 4.01 (m, 1H), 3.93-3.90 (m, 2H), 3.83-3.79 (m, 2H), 3.75 (m, 2H), 3.48-3.46 (m, 1H), 2.07-2.02 (m, 2H). MS (ESI) m/z: Calculated for C21H17F3N6O2: 442.14. found: 443.2 (M+H)+

Sources & evidence

ORD record
ord-b7ba493668334004917e464ac79a6e4d
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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