tert-Butyl [4-(2-aminoethyl)pyridin-2-yl]carbamate → HCID 67243361, compound

HRID 2422128Notes

Reaction equation

HRID 2422128 reaction equation
ClC1C(=O)N(C(C)C)S(=O)(=O)C=1C1C=CC=CC=1.NCCC1C=CN=C(NC(=O)OC(C)(C)C)C=1.[CH:36]([N:39]1[C:43](=[O:44])[C:42]([NH:45][CH2:46][CH2:47][C:48]2[CH:53]=[CH:52][N:51]=[C:50]([NH:54][C:55](=[O:61])[O:56][C:57]([CH3:60])([CH3:59])[CH3:58])[CH:49]=2)=[C:41]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[S:40]1(=[O:69])=[O:68])([CH3:38])[CH3:37].ClC1C(N2CC(N)C2)=NC=C(C(F)(F)F)C=1>>[CH:36]([N:39]1[C:43](=[O:44])[C:42]([NH:45][CH2:46][CH2:47][C:48]2[CH:53]=[CH:52][N:51]=[C:50]([NH:54][C:55](=[O:61])[O:56][C:57]([CH3:60])([CH3:59])[CH3:58])[CH:49]=2)=[C:41]([C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)[S:40]1(=[O:68])=[O:69])([CH3:38])[CH3:37].[NH2:54][C:50]1[CH:49]=[C:48]([CH2:47][CH2:46][NH:45][C:42]2[C:43](=[O:44])[N:39]([CH:36]([CH3:37])[CH3:38])[S:40](=[O:69])(=[O:68])[C:41]=2[C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[CH:53]=[CH:52][N:51]=1

Participants

6

Reactant 4

HCID 22097761tert-Butyl [4-(2-aminoethyl)pyridin-2-yl]carbamateHCID 63761213HCID 63761213, compoundHCID 672431604-Chloro-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxideHCID 86625884HCID 86625884, compound

Product 2

HCID 67243361HCID 67243361, compoundHCID 86625884HCID 86625884, compound

Procedure

The title compound was prepared in two steps. tert-Butyl (4-{2-[(2-isopropyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]ethyl}pyridin-2-yl)carbamate was prepared from 4-chloro-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide and tert-butyl [4-(2-aminoethyl)pyridin-2-yl]carbamate in a similar manner as described for Example 118. Deprotection of tert-butyl (4-{2-[(2-isopropyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]ethyl}pyridin-2-yl)carbamate in a similar manner as described for 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]azetidin-3-amine gave the title compound.

Workup

  1. customThe title compound was prepared in two steps

Sources & evidence

ORD record
ord-bf6a21755c0a4580bd136127e9e63cad
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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