Trifluoroacetic acid → 2-[3-(4-Chlorophenyl)ureido]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide trifluoroacetate

HRID 1483200Notes

Reaction equation

HRID 1483200 reaction equation
[C:1]([C:4]1[C:12]2[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][C:7]=2[S:6][C:5]=1[NH:20][C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)=[O:22])(=[O:3])[NH2:2].[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34]>C(Cl)Cl>[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([NH:23][C:21](=[O:22])[NH:20][C:5]2[S:6][C:7]3[CH2:8][NH:9][CH2:10][CH2:11][C:12]=3[C:4]=2[C:1]([NH2:2])=[O:3])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66662753tert-Butyl 3-carbamoyl-2-[3-(4-chlorophenyl)ureido]-4,5-dihydrothieno[2,3-c]pyridine-6(7H)-carboxylate

Product 1

HCID 1182698802-[3-(4-Chlorophenyl)ureido]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide trifluoroacetateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound A3 (16.0 g, 35.5 mmol) in methylene chloride (100 mL) was added trifluoroacetic acid (30.0 mL, 392 mmol) dropwise over 5 min at 0° C. After the addition complete, the reaction mixture was warmed to room temperature and stirred for 4 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was triturated with ethyl acetate (75 mL) to afford compound A4 as an off-white solid (16.5 g, quantitative yield): 1H NMR (500 MHz, DMSO-d6) δ 10.97 (s, 1H), 10.24 (s, 1H), 9.17 (bs, 2H), 7.60-7.12 (m, 6H), 4.25 (s, 2H), 3.37-3.34 (m, 2H), 3.01-2.98 (m, 2H). MS (M+H) 351.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was triturated with ethyl acetate (75 mL)

Sources & evidence

ORD record
ord-d69dcb2b2d784f7799dc6824b3f07615
Source dataset
uspto-grants-2016_08
Patent number
US09416141B2

Reaction notes

Loading…