5-Morpholinopyridin-3-amine → HCID 59631026, compound

HRID 1431701Notes

Reaction equation

HRID 1431701 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([N:14]2[CH2:18][CH2:17][CH2:16][C@H:15]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:3]=1[CH3:26].[O:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:34]=[C:35]([NH2:39])[CH:36]=[N:37][CH:38]=2)[CH2:29][CH2:28]1>C1(C)C=CC=CC=1>[F:12][C:10]1[CH:9]=[C:8]([F:13])[CH:7]=[C:6]2[C:11]=1[C:2]([NH:39][C:35]1[CH:36]=[N:37][CH:38]=[C:33]([N:30]3[CH2:31][CH2:32][O:27][CH2:28][CH2:29]3)[CH:34]=1)=[C:3]([CH3:26])[C:4]([N:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[N:5]2

Participants

4

Reactant 2

HCID 583477375-Morpholinopyridin-3-amineHCID 59631329HCID 59631329, compound

Product 1

HCID 59631026HCID 59631026, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to Procedure H using (S)-tert-butyl 1-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)pyrrolidine-2-carboxylate (260 mg, 0.68 mmol) and 5-morpholinopyridin-3-amine in toluene to give (S)-tert-butyl 1-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)pyrrolidine-2-carboxylate. 1H NMR (CDCl3) δ ppm 7.80 (1H, d, J=2.2 Hz), 7.65-7.75 (2H, m), 7.07-7.17 (1H, m), 6.90 (1H, br. s.), 6.60 (1H, ddd, J=13.1, 8.8, 2.5 Hz), 4.71 (1H, t, J=7.0 Hz), 3.83-3.94 (1H, m), 3.77-3.83 (4H, m), 3.67-3.77 (1H, m), 3.15-3.26 (4H, m), 2.28-2.43 (1H, m), 2.21 (3H, s), 2.08-2.19 (1H, m), 1.90-2.06 (2H, m), 1.45 (9H, s). Mass Spectrum (ESI) m/e=526.3 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-34ca81911c084acd8557772ade4095f8
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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