2-Amino-4-methylthiazole → (3R-trans)-3,4-Dihydro-3-hydroxy-2,2-dimethyl-4-[(4-methyl-2-thiazolyl)amino]-2H-1-benzopyran-6-carbonitrile

HRID 356664Notes

Reaction equation

HRID 356664 reaction equation
[CH3:1][C:2]1([CH3:15])[C@@H:7]2[O:8][C@@H:6]2[C:5]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:4]=2[O:3]1.C(C1C=CC2OC(C)(C)[C@H](O)[C@@H](N(CC(OCC)=O)C3C=CC=CC=3)C=2C=1)#N.[NH2:44][C:45]1[S:46][CH:47]=[C:48]([CH3:50])[N:49]=1>>[OH:8][C@@H:7]1[C@@H:6]([NH:44][C:45]2[S:46][CH:47]=[C:48]([CH3:50])[N:49]=2)[C:5]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:4]=2[O:3][C:2]1([CH3:15])[CH3:1]

Participants

4

Reactant 3

HCID 741432-Amino-4-methylthiazoleHCID 10738551(3R-trans)-[(6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)phenylamino]acetic acid, ethyl esterHCID 10987295(1aR,7bR)-2,2-Dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrile

Product 1

HCID 10805291(3R-trans)-3,4-Dihydro-3-hydroxy-2,2-dimethyl-4-[(4-methyl-2-thiazolyl)amino]-2H-1-benzopyran-6-carbonitrile

Procedure

The title compound was prepared from (1aR-cis)-1a,7b-dihydro-2,2-dimethyl-2H-oxireno-[c][1]benzopyran-6-carbonitrile (the title A compound of Example 3) and 2-amino-4-methyl-thiazole by the procedure described for the title compound of Example 1. The residue was purified by a flash column to give a colorless solid (730 mg, 58%).

Workup

  1. customThe residue was purified by a flash column

Sources & evidence

ORD record
ord-e22e6eae5ca64f7fb138645d58a42b2b
Source dataset
uspto-grants-1998_11
Patent number
US05837702

Reaction notes

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