(R)-2-(pyridin-2-yl)but-3-yn-2-ol → 9-((R)-3-hydroxy-3-(pyridin-2-yl)but-1-yn-1-yl)-4-methyl-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxamide

HRID 575480Notes

Reaction equation

HRID 575480 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]2[O:6][CH2:7][CH:8]([CH3:19])[C:9]3[S:13][C:12]([C:14]([O:16]CC)=O)=[N:11][C:10]=3[C:4]=2[CH:3]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C@:28]([OH:32])([C:30]#[CH:31])[CH3:29].CC1C2SC(C([O-])=O)=[N:40]C=2C2C=CC=CC=2OC1>>[OH:32][C@:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=1)([CH3:29])[C:30]#[C:31][C:2]1[CH:21]=[CH:20][C:5]2[O:6][CH2:7][CH:8]([CH3:19])[C:9]3[S:13][C:12]([C:14]([NH2:40])=[O:16])=[N:11][C:10]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 42554703(R)-2-(pyridin-2-yl)but-3-yn-2-olHCID 86693327Ethyl 9-bromo-4-methyl-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylateHCID 866935514-Methyl-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate

Product 1

HCID 866935509-((R)-3-hydroxy-3-(pyridin-2-yl)but-1-yn-1-yl)-4-methyl-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxamide

Procedure

Similar to as described in General Procedure G, ethyl 9-bromo-4-methyl-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate was reacted with (R)-2-(pyridin-2-yl)but-3-yn-2-ol to give a diasteromeric mixture of ethyl 94(R)-3-hydroxy-3-(pyridin-2-yl)but-1-yn-1-yl)-4-methyl-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate. Following aminolysis of the ethyl ester (similar to as described in General Procedure M) a diasteromeric mixture of the titled compounds was obtained and separated by Prep HPLC.

Workup

  1. customto give
  2. customwas obtained
  3. customseparated by Prep HPLC

Sources & evidence

ORD record
ord-c2bc06b7ca064a1b8b2a68a514cf8a5b
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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