Cesium carbonate → HCID 20767851, compound

HRID 1825156Notes

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.[CH3:17][NH:18][C:19]([C:21]1[C:29]2[C:24](=[CH:25][C:26]([OH:30])=[CH:27][CH:28]=2)[N:23]([CH2:31][CH3:32])[C:22]=1[CH3:33])=[O:20].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:17][NH:18][C:19]([C:21]1[C:29]2[C:24](=[CH:25][C:26]([O:30][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:27][CH:28]=2)[N:23]([CH2:31][CH3:32])[C:22]=1[CH3:33])=[O:20]

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 20767781HCID 20767781, compound

HCID 221435492-(Azetidin-1-ylcarbonyl)-7-chlorothieno[3,2-b]pyridine

Product 1

HCID 20767851HCID 20767851, compound

Procedure

This material was prepared by the reaction of 2-(azetidin-1-ylcarbonyl)-7-chlorothieno[3,2-b]pyridine 25a with 1-ethyl-6-hydroxy-2-methyl-1H-indole-3-carboxylic acid methylamide 71e and Cs2CO3 in a manner as previously described for example 1. 1H NMR (300 MHz, CDCl3) δ 8.47 (1H, d, J=5.5 Hz), 7.75 (2H, m), 7.16 (1H, d, J=1.7 Hz), 7.01 (1H, dd, J=1.7, 8.4 Hz), 6.56 (1H, d, J=5.5 Hz), 5.91 (1H, bs), 4.59 (2H, m), 4.28 (2H, m), 4.11 (2H, m), 3.05 (3H, d, J=4.0 Hz), 2.72 (3H, s), 2.45 (2H, m), 1.33 (3H, m). LCMS (ESI+) [M+H]/z Calc'd 449, found 449.

Sources & evidence

ORD record: ord-987fbf9fb0d34ddcb3661422dc418b84
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045528B2

Reaction notes

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