Cesium carbonate → 6-{[2-(Azetidin-1-ylcarbonyl)thieno[3,2-b]pyridin-7-yl]oxy}-2-methylbenzo[b]thiophene-3-carboxylic acid (cyclopropylmethyl)amide

HRID 1825225Notes

Reaction equation

HRID 1825225 reaction equation
[N:1]1([C:5]([C:7]2[S:15][C:14]3[C:9](=[N:10][CH:11]=[CH:12][C:13]=3Cl)[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH:17]1([CH2:20][NH:21][C:22]([C:24]2[C:25]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][C:26]=3[S:27][C:28]=2[CH3:29])=[O:23])[CH2:19][CH2:18]1.C([O-])([O-])=O.[Cs+].[Cs+]>>[CH:17]1([CH2:20][NH:21][C:22]([C:24]2[C:25]3[CH:33]=[CH:32][C:31]([O:34][C:13]4[CH:12]=[CH:11][N:10]=[C:9]5[CH:8]=[C:7]([C:5]([N:1]6[CH2:4][CH2:3][CH2:2]6)=[O:6])[S:15][C:14]=45)=[CH:30][C:26]=3[S:27][C:28]=2[CH3:29])=[O:23])[CH2:19][CH2:18]1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 207679226-Hydroxy-2-methylbenzo[b]thiophene-3-carboxylic acid (cyclopropylmethyl)amideHCID 221435492-(Azetidin-1-ylcarbonyl)-7-chlorothieno[3,2-b]pyridine

Product 1

HCID 207678586-{[2-(Azetidin-1-ylcarbonyl)thieno[3,2-b]pyridin-7-yl]oxy}-2-methylbenzo[b]thiophene-3-carboxylic acid (cyclopropylmethyl)amideYield 54%

Procedure

This material was prepared by reacting 2-(azetidin-1-ylcarbonyl)-7-chlorothieno[3,2-b]pyridine 25a (88 mg, 0.35 mmole) with 6-hydroxy-2-methyl-1-benzo[b]thiophene-3-carboxylic acid (cyclopropylmethyl)amide 130a (110 mg, 0.42 mmole) and Cs2CO3 (228 mg, 0.70 mmole) in a manner similar to that previously described for example 1 to give a yellow solid (90 mg, 54%). 1H NMR (DMSO-d6, 300 MHz) δ 8.58 (1H, d, J=5.46 Hz), 8.49 (1H, t, J=5.46 Hz), 7.96 (1H, d, J=2.26 Hz), 7.89 (1H, s), 7.83 (1H, d, J=8.85 Hz), 7.33 (1H, dd, J=2.35, 8.76 Hz), 6.75 (1H, d, J=5.46 Hz), 4.62 (2H, t, J=7.72 Hz), 4.10 (2H, t, J=7.82 Hz), 3.20 (2H, t, J=6.31 Hz), 2.62 (3H, s), 2.35 (2H, m), 1.07 (1H, m), 0.46 (2H, m), 0.26 (2H, m).

Workup

  1. customThis material was prepared

Sources & evidence

ORD record
ord-e0b37e4dd3614835913fc92329459685
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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