(1S,2R)-(-)-1-Amino-2-indanol → 4-[2-((1S,2R)-2-Hydroxy-indan-1-ylamino)-benzooxazol-6-yloxy]-pyridine-2-carboxylic acid methylamide

HRID 1988402Notes

Reaction equation

HRID 1988402 reaction equation
CS([C:4]1[O:5][C:6]2[CH:12]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][N:17]=[C:16]([C:20]([NH:22][CH3:23])=[O:21])[CH:15]=3)[CH:10]=[CH:9][C:7]=2[N:8]=1)=O.[NH2:24][C@H:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][C@H:26]1[OH:34]>CN(C)C(=O)C>[CH3:23][NH:22][C:20]([C:16]1[CH:15]=[C:14]([O:13][C:11]2[CH:10]=[CH:9][C:7]3[N:8]=[C:4]([NH:24][C@H:25]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[CH2:27][C@H:26]4[OH:34])[O:5][C:6]=3[CH:12]=2)[CH:19]=[CH:18][N:17]=1)=[O:21]

Participants

4

Reactant 2

HCID 9866743(1S,2R)-(-)-1-Amino-2-indanolHCID 57725414N-methyl-4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)picolinamide

Product 1

HCID 248219304-[2-((1S,2R)-2-Hydroxy-indan-1-ylamino)-benzooxazol-6-yloxy]-pyridine-2-carboxylic acid methylamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide (17 mg, 0.05 mmol, 1.0 eq) and (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol (30 mg, 0.2 mml, 4.0 eq) in 1 mL of N,N-dimethylacetamide was heated in the microwave at 90° C. for 600 seconds. The crude product was purified by reverse phase prep HPLC to give the title compound. MH==417.0.

Workup

  1. customThe crude product was purified by reverse phase prep HPLC

Sources & evidence

ORD record
ord-28df2d241e6c4f399f93c32506ea9908
Source dataset
uspto-grants-2009_06
Patent number
US07553854B2

Reaction notes

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