Cesium carbonate → HCID 20767830, compound

HRID 1825102Notes

Reaction equation

HRID 1825102 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:16][CH:15]([OH:17])[CH2:14]3)=[O:12])[S:10][C:3]=12.[CH3:18][NH:19][C:20]([C:22]1[C:30]2[C:25](=[CH:26][C:27]([OH:31])=[CH:28][CH:29]=2)[N:24]([CH3:32])[C:23]=1[CH3:33])=[O:21].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:18][NH:19][C:20]([C:22]1[C:30]2[C:25](=[CH:26][C:27]([O:31][C:2]3[CH:7]=[CH:6][N:5]=[C:4]4[CH:8]=[C:9]([C:11]([N:13]5[CH2:16][CH:15]([OH:17])[CH2:14]5)=[O:12])[S:10][C:3]=34)=[CH:28][CH:29]=2)[N:24]([CH3:32])[C:23]=1[CH3:33])=[O:21]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 221435306-hydroxy-N,1,2-trimethyl-1H-indole-3-carboxamideHCID 221435917-Chloro-2-[3-hydroxyazetidin-1-carbonyl]thieno[3,2-b]pyridine

Product 1

HCID 20767830HCID 20767830, compound

Procedure

This material was prepared by the reaction of (7-chloro-thieno [3,2-b]pyridin-2-yl)-(3-hydroxy-azetidin-1-yl)-methanone 9d with 6-hydroxy-1,2-dimethyl-1H-indole-3-carboxylic 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), 7.78–7.74 (2H, m), 7.29 (1H, d, J=2.1 Hz), 6.95(1H, dd, J=2.1, 8.6 Hz), 6.62 (1H, d, J=5.5 Hz), 4.76–4.73 (2H, m), 4.63 (1H, bs), 4.35–4.32 (2H, m), 3.9.7–3.94(1H, m), 3.62(3H, s), 2.89(3H, s), 2.57 (3H, s). LCMS (ESI+) [M+H]/z Calc'd 451. found 451.

Sources & evidence

ORD record
ord-82202adc54184e009413f11235a8f422
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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