Ammonia → HCID 24810340, compound

HRID 2081113Notes

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]([CH2:30][C:31]5[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=5)[C:28]([CH3:39])=[N:27][N:26]=4)[CH:22]=[CH:21][C:20]=3[CH3:40])[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[N:29]([CH2:30][C:31]5[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=5)[C:28]([CH3:39])=[N:27][N:26]=4)[CH:22]=[CH:21][C:20]=3[CH3:40])[C:9]=2[C:10]([NH2:1])=[N:11][CH:12]=1)=[O:6])[CH3:3]

Participants

Conditions

Temperature: 140 °C

Procedure

Ammonia gas was bubbled into a suspension of 4-chloro-3-{5-[4-(4-methoxy-benzyl)-5-methyl-4H-[1,2,4]triazol-3-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (0.330 g; 0.59 mmol) (from Example 58 supra) in 2-propanol (20 mL) for 15-20 minutes. The mixture was then heated in a microwave reactor at 140° C. for 90 minutes. The reaction mixture was concentrated and the residue was purified by flash chromatography (120 g column; 4% methanol in dichloromethane followed by a gradient to 40% methanol) to give 4-amino-3-{5-[4-(4-methoxy-benzyl)-5-methyl-4H-[1,2,4]triazol-3-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (0.263 g; 96% pure; 78.72%).

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by flash chromatography (120 g column

Sources & evidence

ORD record: ord-c7ccc10486cc448087885a785f995c79
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932390B2

Reaction notes

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