Azetidine → HCID 90067476, compound

HRID 1057027Notes

Reaction equation

HRID 1057027 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]([C:21]2([C:27]#[N:28])[CH2:26][CH2:25][O:24][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]([C:21]3([C:27]#[N:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH:7]=2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 10422AzetidineHCID 72550495HCID 72550495, compound

Product 1

HCID 90067476HCID 90067476, compoundYield 17%

Procedure

Reaction of azetidine with 2-((6-chloro-4-(4-cyanotetrahydro-2H-pyran-4-yl)pyridin-2-yl)amino)isonicotinonitrile (50.0 mg, 0.147 mmol) following procedure of Method A afforded the target compound as a colorless solid (8.9 mg, 17%); 1H NMR (400 MHz, DMSO) δ 9.95 (br s, 1H), 8.48 (s, 1H), 8.42 (d, J=5.0 Hz, 1H), 7.23 (dd, J=5.0, 1.4 Hz, 1H), 6.89 (d, J=1.2 Hz, 1H), 5.99 (d, J=1.2 Hz, 1H), 4.06-3.98 (m, 6H), 3.70-3.59 (m, 2H), 2.41-2.28 (m, 2H), 2.08-1.96 (m, 4H); ESI-LRMS m/z [M+1]+=361.

Sources & evidence

ORD record
ord-c95abe2ce93547b88d02767863de1d27
Source dataset
uspto-grants-2016_07
Patent number
US09399636B2

Reaction notes

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