Trifluoroacetic anhydride → 3-(2'-amino-2-phenyl-5'H-spiro[chroman-4,4'-thiazole]-6-yl)benzonitrile

HRID 2096624Notes

Reaction equation

HRID 2096624 reaction equation
[NH2:1][C:2]1[S:3][CH2:4][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]4[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=4)[C:19]([NH2:21])=O)[CH:14]=3)[O:9][CH:8]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:7]2)[N:6]=1.CCN(C(C)C)C(C)C.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C:2]1[S:3][CH2:4][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]4[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=4)[C:19]#[N:21])[CH:14]=3)[O:9][CH:8]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:7]2)[N:6]=1

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 81531DiisopropylethylamineHCID 584244103-(2'-amino-2-phenyl-5'H-spiro[chroman-4,4'-thiazole]-6-yl)benzamide

Product 1

HCID 671739113-(2'-amino-2-phenyl-5'H-spiro[chroman-4,4'-thiazole]-6-yl)benzonitrileYield 8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2′-amino-2-phenyl-5′H-spiro[chroman-4,4′-thiazole]-6-yl)benzamide (20 mg, 0.048 mmol) and DIEA (21 mg, 0.096 mmol) in CH2Cl2 was added TFAA (0.2 mL) at 0° C. The mixture was stirred at room temperature for 1 h and concentrated to give the residue, which was purified by preparative TLC to give 3-(2′-amino-2-phenyl-5′H-spiro[chroman-4,4′-thiazole]-6-yl)benzonitrile (1.53 mg, 8%). 1H-NMR (MeOD): 2.27 (m, 2H), 3.36 (m, 1H), 3.84 (m, 1H), 5.24 (m, 1H), 6.92 (m, 1H), 7.31 (m, 4H), 7.48 (m, 4H), 7.81 (m, 3H).

Workup

  1. concentrationconcentrated
  2. customto give the residue, which
  3. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-b2fdf1c8f2ae4a7fb8f2a23e7936d0f8
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

Loading…