Ammonia → N-(3-Aminophenyl)-3-[(quinolin-4-ylmethyl)amino]thiophene-2-carboxamide

HRID 1171890Notes

Reaction equation

HRID 1171890 reaction equation
COC1C(=O)C(=O)C=1[NH:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]([C:19]2[S:20][CH:21]=[CH:22][C:23]=2[NH:24][CH2:25][C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[O:18])[CH:13]=[CH:14][CH:15]=1.N>CS(C)=O.CO>[NH2:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]([C:19]2[S:20][CH:21]=[CH:22][C:23]=2[NH:24][CH2:25][C:26]2[C:27]3[C:28](=[CH:11][CH:10]=[CH:15][CH:14]=3)[N:29]=[CH:30][CH:31]=2)=[O:18])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86605118N-{3-[(2-methoxy-3,4-dioxocyclobut-1-en-1-yl)amino]phenyl}-3-[(pyridin-4-ylmethyl)amino]thiophene-2-carboxamide

Product 1

HCID 59814810N-(3-Aminophenyl)-3-[(quinolin-4-ylmethyl)amino]thiophene-2-carboxamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

To a solution of N-{3-[(2-methoxy-3,4-dioxocyclobut-1-en-1-yl)amino]phenyl}-3-[(pyridin-4-ylmethyl)amino]thiophene-2-carboxamide (EXAMPLE 1) (50 mg, 0.01 mmol) in DMSO (150 μL) was added a 2M solution of ammonia in methanol (650 μL). The reaction was left for 6 h at rt. The reaction was then purified by reverse phase HPLC using a gradient of 5→65% MeCN/H2O over 15 min at 15 mL/min. Removal of the solvent provided EXAMPLE 3 as a white solid. MS (ES): m/z 469.9 [MH+]. 1H NMR (DMSO-d6, 400 MHz): δ=5.06 (d, J=6.0 Hz, 2H), 6.82 (d, J=5.6 Hz, 1H), 7.18 (d, J=8.0 Hz, 1H), 7.25 (t, J=8.4 Hz, 1H), 7.37 (d, J=7.6 Hz, 1H), 7.39 (d, J=4.4 Hz, 1H), 7.61 (d, J=5.2 Hz, 1H), 7.64-7.68 (m, 2H), 7.78 (t, J=7.2 Hz, 1H), 8.02-8.06 (m, 2H), 8.21 (d, J=8.4 Hz, 1H), 8.83 (d, J=4.4 Hz, 1H), 9.48 (s, 1H), 9.78 (s, 1H).

Workup

  1. customThe reaction was then purified by reverse phase HPLC
  2. customover 15 min
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-5b5ace105a3c4b99ac5636ffe32523f4
Source dataset
uspto-grants-2010_11
Patent number
US07829717B2

Reaction notes

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