2-Amino-4,5-dichloro-3-nitropyridine → HCID 117702007, compound
Reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]([NH2:9])[C:3]=1[N+:10]([O-:12])=[O:11].[NH2:13][C@@H:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]1[NH:20][S:21]([CH3:24])(=[O:23])=[O:22]>>[NH2:9][C:4]1[C:3]([N+:10]([O-:12])=[O:11])=[C:2]([NH:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]2[NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[C:7]([Cl:8])=[CH:6][N:5]=1Participants
Procedure
In a similar fashion as for the synthesis of Compound A (X═Cl), 4,5-dichloro-3-nitro-pyridin-2-ylamine was reacted with N-((1R,2R)-2-amino-cyclohexyl)-methanesulfonamide to afford N-[(1R,2R)-2-(2-amino-5-chloro-3-nitro-pyridin-4-ylamino)-cyclohexyl]-methanesulfonamide (72%) which was subjected to hydrogenation with iron in acetic acid in a similar fashion as for Compound B to afford N-[(1R,2R)-2-(2,3-diamino-5-chloro-pyridin-4-ylamino)-cyclohexyl]-methanesulfonamide (66%). This latter material was then reacted with 2-methoxy-4-morpholin-4-ylmethyl-benzaldehyde in a similar fashion as for the synthesis of Compound III to afford the title compound as a yellow lyophilate (70%). 1H NMR (d-chloroform): 13.39 (br s, 1H), 8.30 (d, J=8 Hz, 1H), 8.23 (s, 1H), 7.19 (m, 1H), 7.12 (s, 1H), 7.03 (d, J=8 Hz, 1H), 6.76 (d, J=8 Hz, 1H), 5.05 (m, 1H), 4.97 (m, 1H), 4.12-3.81 (m, 6H), 3.64 (s, 3H), 3.48 (m, 1H), 3.25 (m, 1H), 3.12 (s, 3H), 3.06 (m, 1H), 2.83 (m, 1H), 2.22 (m, 2H), 2.01-1.60 (m, 4H), 1.44 (m, 2H), 1.25 (m, 1H). MS: 549.0 (M+H). HPLC retention time: 1.85 minutes (G Method).
Sources & evidence
- ORD record
- ord-df3527ab95a840398d0dc12780f3480f
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238656B2
Reaction notes
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