Tert-butyl (4-methyl-5-nitropyridin-2-yl)carbamate → tert-butyl (5-amino-4-methylpyridin-2-yl)(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)carbamate

HRID 1039075Notes

Reaction equation

HRID 1039075 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][C@@H:14]2[CH2:16][C@@H:15]2[CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[N:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=3)[CH2:19][CH2:18]2)(=O)=O)=CC=1.[CH3:30][C:31]1[C:36]([N+:37]([O-])=O)=[CH:35][N:34]=[C:33]([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH:32]=1>>[NH2:37][C:36]1[C:31]([CH3:30])=[CH:32][C:33]([N:40]([CH2:12][CH2:13][C@@H:14]2[CH2:16][C@@H:15]2[CH:17]2[CH2:18][CH2:19][N:20]([C:23]3[N:24]=[CH:25][C:26]([Cl:29])=[CH:27][N:28]=3)[CH2:21][CH2:22]2)[C:41](=[O:47])[O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[N:34][CH:35]=1

Participants

3

Reactant 2

HCID 67962197Tert-butyl (4-methyl-5-nitropyridin-2-yl)carbamateHCID 866661412-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl 4-methylbenzenesulfonate

Product 1

HCID 67962339tert-butyl (5-amino-4-methylpyridin-2-yl)(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)carbamate

Procedure

The title compound was synthesized by procedure analogous to Step 2 and 3 of Example 28 from 2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl 4-methylbenzenesulfonate from Step 1 of Example 5 and tert-butyl (4-methyl-5-nitropyridin-2-yl)carbamate from Step 1 of this example.

Sources & evidence

ORD record
ord-89de2f729d8f4eb3af18d7b0f3e93015
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

Loading…