Ammonia → HCID 24810336, compound

HRID 2081110Notes

Reaction equation

HRID 2081110 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:29][N:28]=[C:27]([CH3:30])[N:26]=4)[CH:22]=[CH:21][C:20]=3[CH3:31])[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:29][N:28]=[C:27]([CH3:30])[N:26]=4)[CH:22]=[CH:21][C:20]=3[CH3:31])[C:9]=2[C:10]([NH2:1])=[N:11][CH:12]=1)=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 24810335HCID 24810335, compound

Product 1

HCID 24810336HCID 24810336, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
140 °C

Procedure

Ammonia gas was bubbled into a solution of 4-chloro-3-[2-methyl-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (0.42 g, 0.95 mmol) (from Example 53 supra) in 2-propanol (30 mL) for 20 minutes. The mixture was heated in a microwave reactor at 140° C. for 2 hours. The reaction mixture was concentrated. The residue washed with hot methanol, filtered and dried to give 4-amino-3-[2-methyl-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester as a white powder. (Yield 0.33 g, 83%).

Workup

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

Sources & evidence

ORD record
ord-25411536b5604f1fb49b9319a6727a6c
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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