5-Chloro-2-thiophenecarboxylic acid → HCID 24760601, compound

HRID 1802601Notes

Reaction equation

HRID 1802601 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:37][CH2:38][C:39]1[N:40]=[CH:41][N:42]([C:44]2[CH:53]=[CH:52][C:51]([N:54]3[CH:59]=[CH:58][CH:57]=[CH:56][C:55]3=[O:60])=[CH:50][C:45]=2[C:46]([O:48][CH3:49])=[O:47])[CH:43]=1>CN(C=O)C>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:37][CH2:38][C:39]2[N:40]=[CH:41][N:42]([C:44]3[CH:53]=[CH:52][C:51]([N:54]4[CH:59]=[CH:58][CH:57]=[CH:56][C:55]4=[O:60])=[CH:50][C:45]=3[C:46]([O:48][CH3:49])=[O:47])[CH:43]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 950485-Chloro-2-thiophenecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66974247HCID 66974247, compound

Product 1

HCID 24760601HCID 24760601, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chlorothiophene-2-carboxylic acid 1-5 (40 mg, 0.25 mmol) and TEA (0.068 mL, 0.49 mmol) in DMF (2 mL), BOP (142 mg, 0.32 mmol) was added. After 5 min of mixing, the solution was added to the sample methyl 2-(4-(aminomethyl)-1H-imidazol-1-yl)-5-(2-oxopyridin-1(2H)-yl)benzoate prepared above. The mixture was then stirred at room temperature for 1 h before it was purified by HPLC to give the title compound (4 mg). MS 469.0 and 471.0 (M+H, Cl pattern).

Workup

  1. additionAfter 5 min of mixing
  2. customprepared above
  3. customwas purified by HPLC

Sources & evidence

ORD record
ord-034906f3a46c47c0a48629f8de0a8857
Source dataset
uspto-grants-2013_01
Patent number
US08349873B2

Reaction notes

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