Ammonia → HCID 178469826, compound

HRID 2081116Notes

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[N:29](C)[CH:28]=[N:27][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].[CH3:32]C(O)C>ClCCl>[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[NH:29][C:28]([CH3:32])=[N:27][N:26]=4)[CH:22]=[CH:21][C:20]=3[CH3:31])[C:9]=2[C:10]([NH2:11])=[N:1][CH:12]=1)=[O:6])[CH3:3]

Participants

Conditions

Temperature: 140 °C

Procedure

Ammonia gas was bubbled into a suspension of 4-chloro-3-[2-methyl-5-(methyl-4H-[1,2,4]triazol-3-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (0.106 g; 0.24 mmol) (from Example 61 supra) in 2-propanol (20 mL) for 15-20 minutes. The mixture was then heated in a microwave reactor at 140° C. for 75 minutes. After cooling to room temperature the reaction mixture was diluted with dichloromethane (˜75 mL) and washed with water and then brine. The organic phase was dried (Na2SO4) and concentrated. The residue was triturated twice with hot dichloromethane to give 4-amino-3-[2-methyl-5-(5-methyl-4H-[1,2,4]triazol-3-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester as a white solid. (Yield 80.4 mg) Additional product was obtained by chromatographing the mother liquors from the two triturations. (Yield 7.7 mg, overall 82.49%).

Workup

temperatureAfter cooling to room temperature the reaction mixture
washwashed with water
dry with materialThe organic phase was dried (Na2SO4)
concentrationconcentrated
customThe residue was triturated twice with hot dichloromethane

Sources & evidence

ORD record: ord-a15068b8a3a04b8180ea32416d15d52c
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932390B2

Reaction notes

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