Azetidine → HCID 72547727, compound

HRID 1057033Notes

Reaction equation

HRID 1057033 reaction equation
[NH:1]1[CH2:4][CH2:3][CH2:2]1.Cl[C:6]1[N:11]=[C:10]([NH:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][N:20]=2)[C:16]#[N:17])[CH:9]=[C:8]([CH:21]2[CH2:26][CH2:25][N:24]([CH:27]3[CH2:30][O:29][CH2:28]3)[CH2:23][CH2:22]2)[CH:7]=1>>[N:1]1([C:6]2[N:11]=[C:10]([NH:12][C:13]3[CH:14]=[C:15]([CH:18]=[CH:19][N:20]=3)[C:16]#[N:17])[CH:9]=[C:8]([CH:21]3[CH2:22][CH2:23][N:24]([CH:27]4[CH2:30][O:29][CH2:28]4)[CH2:25][CH2:26]3)[CH:7]=2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 10422AzetidineHCID 72547722HCID 72547722, compound

Product 1

HCID 72547727HCID 72547727, compoundYield 47%

Procedure

Reaction of azetidine with 2-((6-chloro-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridin-2-yl)amino)isonicotinonitrile (40 mg, 0.11 mmol) following general Buchwald-Hartwig procedure described above afforded the target compound as a colorless solid (19.8 mg, 47%); 1H NMR (400 MHz, DMSO) δ 9.76 (br s, 1H), 8.51 (s, 1H), 8.40 (d, J=5.1 Hz, 1H), 7.18 (d, J=5.1 Hz, 1H), 6.59 (s, 1H), 5.80 (s, 1H), 4.57-4.49 (m, 2H), 4.49-4.40 (m, 2H), 4.00-3.92 (m, 4H), 3.43-3.35 (m, 1H), 2.82-2.73 (m, 2H), 2.40-2.27 (m, 3H), 1.88-1.78 (m, 2H), 1.77-1.68 (m, 2H), 1.68-1.51 (m, 2H); ESI-LRMS m/z [M+1]+=391.

Sources & evidence

ORD record
ord-21ce8af432bd4530b8e717a1f2b1585c
Source dataset
uspto-grants-2016_07
Patent number
US09399636B2

Reaction notes

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