Cesium carbonate → HCID 69368700, compound

HRID 1825095Notes

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]([CH3:31])[C:22]=1[CH3:32])=[O:20].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:17][NH:18][C:19]([CH: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]([CH3:31])[CH:22]1[CH3:32])=[O:20]

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 221435306-hydroxy-N,1,2-trimethyl-1H-indole-3-carboxamide

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

Product 1

HCID 69368700HCID 69368700, compound

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-carbyxylic acid methylamide 16e and Cs2CO3 in a manner as previously described for example 1. 1H NMR (300 MHz, CD3OD) δ 8.41 (1H, d, J=5.5 Hz), 7.80 (1H, d, J=3.20 Hz), 7.74 (1H, d, J=11.68 Hz), 7.30 (1H, s), 6.94 (1H, d, J=8.66 Hz), 6.62 (1H, d, J=5.5 Hz), 4.64–4.59 (2H, m), 4.20–4.15 (2H, m), 3.63 (3H, s), 2.85 (3H, s), 2.57 (3H, s), 2.44–2.36 (2H, m). LCMS (ESI+) [M+H]/z Calc'd 435. found 435.

Sources & evidence

ORD record: ord-5d6f9b57548c480b926dc6d4353068eb
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045528B2

Reaction notes

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