Trifluoroacetic acid → 7-Aminonaphtho[2,1-d]thiazole-2-carbonitrile

HRID 64514

Reaction equation

HRID 64514 reaction equation
[C:1]([C:3]1[S:4][C:5]2[C:15]3[C:10](=[CH:11][C:12]([NH:16]C(=O)OC(C)(C)C)=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].C1(SC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[C:5]1[S:4][C:3]([C:1]#[N:2])=[N:7][C:6]=1[CH:8]=[CH:9]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 131737225tert-Butyl (2-cyanonaphtho[2,1-d]thiazol-7-yl)carbamate

Product 1

HCID 1176042347-Aminonaphtho[2,1-d]thiazole-2-carbonitrileYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl (2-cyanonaphtho[2,1-d]thiazol-7-yl)carbamate (72 mg, 0.22 mmol) and thioanisole (0.5 mL) in 2 mL of DCM in an ice bath, 2 mL of trifluoroacetic acid was added. After 1 h, the reaction was concentrated under reduced pressure, and the product (47 mg, 94%) was isolated by silica gel chromatography eluting with 0→75% EtOAc in heptanes. 1H NMR (CD2Cl2) d 8.01 (d, 1H); 7.90 (dt, 1H); 7.76 (d, 1H); 7.09-7.16 (m, 2H).

Workup

  1. concentrationthe reaction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-322ac2bbe2cc4c8b95d0a482635efc12
Source dataset
uspto-grants-2016_09
Patent number
US09447450B2

Linked notes

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