Trifluoroacetic acid → 6-(4-(Benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)picolinic acid

HRID 1641077Notes

Reaction equation

HRID 1641077 reaction equation
FC(F)(F)C(O)=O.[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:17][C:18]([N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([C:30]3[N:35]=[C:34]([C:36]([O:38]C(C)(C)C)=[O:37])[CH:33]=[CH:32][CH:31]=3)[CH:28]=2)[N:23]([CH3:43])[CH2:22][CH2:21]1)=[O:19]>C(Cl)Cl>[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:17][C:18]([N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([C:30]3[N:35]=[C:34]([C:36]([OH:38])=[O:37])[CH:33]=[CH:32][CH:31]=3)[CH:28]=2)[N:23]([CH3:43])[CH2:22][CH2:21]1)=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59418667Tert-butyl 6-(4-(benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)picolinate

Product 1

HCID 468409196-(4-(Benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)picolinic acidYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound 6-(4-(benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)picolinic acid (25) was prepared by the following procedure: Trifluoroacetic acid (2.0 mL) was added dropwise to tert-butyl 6-(4-(benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)picolinate (25H) (79 mg, 0.16 mmol) in DCM (2.0 mL) at 0° C. The mixture was allowed to warm up to rt and stirred for 72 hours. The mixture was concentrated, triturated with diethylether, filtered, and dried in vacuo to provide 62 mg (70%) of the desired product 6-(4-(benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)picolinic acid (25): 1H NMR (300 MHz, DMSO-d6) δ 8.28 (1H, s), 8.01-7.72 (5H, m), 7.45-7.30 (2H, m), 7.21 (1H, t), 6.82 (1H, d), 4.03 (2H, t), 3.45 (2H, t), 3.00 (3H, s). MS (ESI(+)): m/z 446.0 (M+H).

Workup

  1. customThe title compound 6-(4-(benzo[d]thiazol-2-ylcarbamoyl)-1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)picolinic acid (25) was prepared by the following procedure
  2. concentrationThe mixture was concentrated
  3. customtriturated with diethylether
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-72f7374482c047519c9661de2f3ef94b
Source dataset
uspto-grants-2012_02
Patent number
US08114893B2

Reaction notes

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