Trifluoroacetic acid → HCID 46841188, compound

HRID 2178264Notes

Reaction equation

HRID 2178264 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]([OH:38])=[O:37])[C:33]([C:39]4[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][O:46][C:47]5[CH:52]=[CH:51][CH:50]=[C:49]([NH:53]C(OC(C)(C)C)=O)[CH:48]=5)[CH:40]=4)=[CH:32][CH:31]=3)[CH:28]=2)[CH2:23][CH2:22][CH2:21]1)=[O:19]>C(Cl)Cl>[NH2:53][C:49]1[CH:48]=[C:47]([CH:52]=[CH:51][CH:50]=1)[O:46][CH2:45][C:41]1[CH:40]=[C:39]([C:33]2[C:34]([C:36]([OH:38])=[O:37])=[N:35][C:30]([C:27]3[CH:28]=[C:29]4[C:24]([CH2:23][CH2:22][CH2:21][N:20]4[C:18](=[O:19])[NH:17][C:9]4[S:8][C:12]5[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=5[N:10]=4)=[CH:25][CH:26]=3)=[CH:31][CH:32]=2)[CH:44]=[CH:43][CH:42]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 46841757HCID 46841757, compound

Product 1

HCID 46841188HCID 46841188, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound 3-(3-((3-aminophenoxy)methyl)phenyl)-6-(1-(benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)picolinic acid (34) was prepared by the following procedure: Trifluoroacetic acid (0.5 mL) was added to a solution of 6-(1-(benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)-3-(3-((3-(tert-butoxycarbonylamino)phenoxy)methyl)phenyl)picolinic acid (34E) (0.016 g, 0.022 mmol) in anhydrous DCM (0.75 mL). The reaction mixture was stirred at rt for 1.5 hours, concentrated under reduced pressure, and the crude material triturated in diethyl ether to provide the desired product 3-(3-((3-aminophenoxy)methyl)phenyl)-6-(1-(benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)picolinic acid (34): 1H NMR (300 MHz, DMSO) δ 8.43 (1H, s, br), 8.08 (1H, d), 7.99 (1H, d), 7.85-7.77 (2H, m), 7.67 (1H, s), 7.55-7.41 (4H, m), 7.37 (1H, t), 7.31 (1H, d), 7.22 (1H, t), 7.12 (1H, t), 6.59-7.50 (2H, m), 6.47 (1H, d), 5.11 (2H, s), 3.97 (2H, t), 2.84 (2H, t), 1.96 (2H, m). MS (ESI(+)) m/z 628.1 (M+H).

Workup

  1. customThe title compound 3-(3-((3-aminophenoxy)methyl)phenyl)-6-(1-(benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)picolinic acid (34) was prepared by the following procedure
  2. concentrationconcentrated under reduced pressure
  3. customthe crude material triturated in diethyl ether

Sources & evidence

ORD record
ord-16693d6b6a0e4c9fafc34d21be4aaca8
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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