Cesium carbonate → 6-[2-(Azetidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-1,2-dimethyl-1H-indole-3-carboxylic acid (3-hydroxy-propyl)-amide

HRID 985259Notes

Reaction equation

HRID 985259 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.[OH:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([C:24]1[C:32]2[C:27](=[CH:28][C:29]([OH:33])=[CH:30][CH:31]=2)[N:26]([CH3:34])[C:25]=1[CH3:35])=[O:23].C([O-])([O-])=O.[Cs+].[Cs+]>>[OH:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([C:24]1[C:32]2[C:27](=[CH:28][C:29]([O:33][C:13]3[CH:12]=[CH:11][N:10]=[C:9]4[CH:8]=[C:7]([C:5]([N:1]5[CH2:4][CH2:3][CH2:2]5)=[O:6])[S:15][C:14]=34)=[CH:30][CH:31]=2)[N:26]([CH3:34])[C:25]=1[CH3:35])=[O:23]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 207678646-Hydroxy-1,2-dimethyl-1H-indole-3-carboxylic acid (3-hydroxy-propyl)-amideHCID 221435492-(Azetidin-1-ylcarbonyl)-7-chlorothieno[3,2-b]pyridine

Product 1

HCID 207678566-[2-(Azetidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-1,2-dimethyl-1H-indole-3-carboxylic acid (3-hydroxy-propyl)-amide

Procedure

This material was prepared by the reaction of 2-(azetidin-1-ylcarbonyl)-7-chlorothieno[3,2-b]pyridine 25a with 6-hydroxy-1,2-dimethyl-1H-indole-3-carboxylic acid (3-hydroxy-propyl)-amide 63b and Cs2CO3 in a manner as previously described for example 1. 1H NMR (300 MHz, CD3OD) δ8.50 (1H, d, J=5.5 Hz), 7.89 (1H, d, J=8.7 Hz), 7.82 (1H, s), 7.40 (1H, s), 7.06 (1H, d, J=6.6 Hz), 6.72 (1H, d, J=5.5 Hz), 4.74-4.65 (2H, m), 4.31-3.68 (5H, m), 3.60-3.55 (2H, m), 2.68 (3H, s), 2.54-2.46 (2H, m), 1.95-1.87 (2H, m). LCMS (ESI+) [M+H]/z Calc'd 478, found 478.

Sources & evidence

ORD record
ord-a16af5106c5c43f580200eac78561cf2
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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