Ethylamine → (3R-trans)-2[N-(6-Cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)phenylamino]-N-ethylacetamide

HRID 356662Notes

Reaction equation

HRID 356662 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C@H:9]([OH:14])[C@@H:8]([N:15]([CH2:22][C:23](OCC)=[O:24])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:7]=2[CH:28]=1)#[N:2].[CH2:29]([NH2:31])[CH3:30]>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C@H:9]([OH:14])[C@@H:8]([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:22][C:23]([NH:31][CH2:29][CH3:30])=[O:24])[C:7]=2[CH:28]=1)#[N:2]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 10738551(3R-trans)-[(6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)phenylamino]acetic acid, ethyl ester2×

Product 1

HCID 10547747(3R-trans)-2[N-(6-Cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)phenylamino]-N-ethylacetamide

Procedure

The title compound was prepared from (3R-trans)-[(6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)phenylamino]acetic acid, ethyl ester (the title compound of Example 3) and ethyl amine by the same procedure as described for the title compound of Example 7. The product was triturated with hexanes to give the title compound as a colorless solid, mp 213°-215° C. Analysis calculated for C22H25N3O3 : C, 69.64; H, 6.64; N, 11.07. Found: C, 69.31; H, 6.33; N, 10.96. [α]D =+76.6° (c=0.47, CDCl3).

Workup

  1. customThe product was triturated with hexanes

Sources & evidence

ORD record
ord-b33509508a6b42619afba4ec92613fd3
Source dataset
uspto-grants-1998_11
Patent number
US05837702

Reaction notes

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