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

HRID 1039076Notes

Reaction equation

HRID 1039076 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.[N+:30]([C:33]1[CH:34]=[CH:35][C:36]([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[N:37][CH:38]=1)([O-])=O>>[NH2:30][C:33]1[CH:34]=[CH:35][C:36]([N:39]([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:40](=[O:46])[O:41][C:42]([CH3:44])([CH3:43])[CH3:45])=[N:37][CH:38]=1

Participants

3

Reactant 2

HCID 11064480tert-Butyl (5-nitropyridin-2-yl)carbamateHCID 866661412-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl 4-methylbenzenesulfonate

Product 1

HCID 67962351tert-butyl (5-amino-pyridin-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 (5-nitropyridin-2-yl)carbamate from Step 1 of this example.

Sources & evidence

ORD record
ord-ceeea9d2f61e4298bcab5b6328e1478a
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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