tert-butyl N-((2R)-3-hydroxy-2-methylpropyl)carbamate → 3-[2-[(2R)-3-(t-Butoxycarbonylamino)-2-methylpropoxy]-4-methylthiobenzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide

HRID 1434849Notes

Reaction equation

HRID 1434849 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[C:16]([NH:17][C:18](=[S:27])[C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:20]=3[OH:26])=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:10])=[N:6][CH:7]=1.[C:28]([O:32][C:33]([NH:35][CH2:36][C@@H:37]([CH3:40])[CH2:38]O)=[O:34])([CH3:31])([CH3:30])[CH3:29]>>[C:28]([O:32][C:33]([NH:35][CH2:36][C@@H:37]([CH3:40])[CH2:38][O:26][C:20]1[CH:21]=[C:22]([CH3:25])[CH:23]=[CH:24][C:19]=1[C:18]([NH:17][C:16]1[C:11]([C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)=[O:10])=[N:12][CH:13]=[CH:14][CH:15]=1)=[S:27])=[O:34])([CH3:31])([CH3:30])[CH3:29]

Participants

3

Reactant 2

HCID 10655267tert-butyl N-((2R)-3-hydroxy-2-methylpropyl)carbamateHCID 136348818N-(5-chloropyridin-2-yl)-3-[2-hydroxy-4-methylthiobenzoylamino]pyridine-2-carboxamide

Product 1

HCID 866200063-[2-[(2R)-3-(t-Butoxycarbonylamino)-2-methylpropoxy]-4-methylthiobenzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamideYield 81%

Procedure

Using a procedure analogous to Example 38-D, N-(5-chloropyridin-2-yl)-3-[2-hydroxy-4-methylthiobenzoyl-amino]pyridine-2-carboxamide and (2R)-3-(t-butoxycarbonyl-amino)-2-methylpropanol gave the desired product as a solid (850 mg, 81%).

Sources & evidence

ORD record
ord-dedd91480a4d40898cec950226e9b991
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

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