2-Chloronicotinamide → 2-((S)-3-((1R,2R)-2-(3-Phenylureido)cyclohexylamino)piperidin-1-yl)nicotinamide

HRID 2370013Notes

Reaction equation

[C:1]1([NH:7][C:8]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[NH:17][CH:18]2[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:25]1[N:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([NH2:29])=[O:28]>>[C:1]1([NH:7][C:8](=[O:9])[NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[NH:17][C@H:18]2[CH2:23][CH2:22][CH2:21][N:20]([C:25]3[N:33]=[CH:32][CH:31]=[CH:30][C:26]=3[C:27]([NH2:29])=[O:28])[CH2:19]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 825882-Chloronicotinamide

HCID 712273541-phenyl-3-((1R,2R)-2-(piperidin-3-ylamino)cyclohexyl)urea2×

Product 1

HCID 712267922-((S)-3-((1R,2R)-2-(3-Phenylureido)cyclohexylamino)piperidin-1-yl)nicotinamide

Procedure

2-((S)-3-((1R,2R)-2-(3-Phenylureido)cyclohexylamino)piperidin-1-yl)nicotinamide was synthesized using 1-phenyl-3-((1R,2R)-2-(piperidin-3-ylamino)cyclohexyl)urea (from intermediate C, Example 1) (100 mg, 0.32 mmol) and 2-chloronicotinamide (49 mg, 0.32 mmol) according to General Procedure A to give 9 mg (6.5%) of pale brown oil. Anal. Calcd. for C24H32N6O2 m/z 436.3, found: 437.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 8.2 (d, J=3.8 Hz, 1H), 7.65 (dd, J=2 Hz, 1H), 7.21 (m, 4H), 7.01 (m, 1H), 6.86 (m, 1H), 3.66 (m, 4H), 3.21 (m, 3H), 2.35 (m, 1H), 2.10 (m, 2H), 1.89 (m, 4H), 1.74 (m, 1H), 1.68 (d, J=1.68 Hz, 1H), 1.60 (m, 1H), 1.45 (m, 3H).

Sources & evidence

ORD record: ord-6751bb7ce91744c39664031306375c65
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710049B2

Reaction notes

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