Ammonia → HCID 24810287, compound

HRID 2081104Notes

Reaction equation

HRID 2081104 reaction equation
[NH3:1].[CH2:2]([O:4][C:5]([C:7]1[C:8]2[S:16][CH:15]=[C:14]([CH2:17][O:18][C:19]3[CH:24]=[C:23]([C:25]4[O:26][C:27]([C:30]5[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=5)=[N:28][N:29]=4)[CH:22]=[CH:21][C:20]=3[CH3:37])[C:9]=2[C:10](Cl)=[N:11][CH:12]=1)=[O:6])[CH3:3]>CC(O)C>[CH2:2]([O:4][C:5]([C:7]1[C:8]2[S:16][CH:15]=[C:14]([CH2:17][O:18][C:19]3[CH:24]=[C:23]([C:25]4[O:26][C:27]([C:30]5[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=5)=[N:28][N:29]=4)[CH:22]=[CH:21][C:20]=3[CH3:37])[C:9]=2[C:10]([NH2:1])=[N:11][CH:12]=1)=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 24810286HCID 24810286, compound

Product 1

HCID 24810287HCID 24810287, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
140 °C

Procedure

Ammonia gas was bubbled into a solution of 4-chloro-3-{5-[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (0.30 g, 0.56 mmol) (from Example 46 supra) in 2-propanol (30 mL) for 20 minutes. The mixture was heated in a microwave reactor at 140° C. for 5.5 hours. The reaction mixture was concentrated. The residue washed with hot methanol, filtered and dried to give 4-amino-3-{5-[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester. (Yield 0.22 g, 76%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washThe residue washed with hot methanol
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-bbcebfa652ba4e66b14b154c18013531
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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