Cesium carbonate → HCID 20767920, compound

HRID 1825131Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][CH:13]=[C:14]([C:16]([OH:19])([CH3:18])[CH3:17])[N:15]=3)[S:10][C:3]=12.[CH:20]1([CH2:23][NH:24][C:25]([C:27]2[C:35]3[C:30](=[CH:31][C:32]([OH:36])=[CH:33][CH:34]=3)[N:29]([CH3:37])[C:28]=2[CH3:38])=[O:26])[CH2:22][CH2:21]1.C([O-])([O-])=O.[Cs+].[Cs+]>>[CH:20]1([CH2:23][NH:24][C:25]([C:27]2[C:35]3[C:30](=[CH:31][C:32]([O:36][C:2]4[CH:7]=[CH:6][N:5]=[C:4]5[CH:8]=[C:9]([C:11]6[S:12][CH:13]=[C:14]([C:16]([OH:19])([CH3:18])[CH3:17])[N:15]=6)[S:10][C:3]=45)=[CH:33][CH:34]=3)[N:29]([CH3:37])[C:28]=2[CH3:38])=[O:26])[CH2:22][CH2:21]1

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 22143515HCID 22143515, compound

HCID 221436652-[2-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-thiazol-4-yl]-propan-2-ol

Product 1

HCID 20767920HCID 20767920, compound

Procedure

This material was prepared by the reaction of 2-[2-(7-chlorothieno[3,2-b]pyridin-2-yl)-1,3-thiazol-4-yl]propan-2-ol 40a (0.102 g, 0.33 mmole) with N-(cyclopropylmethyl)-6-hydroxy-1,2-dimethyl-1H-indole-3-carboxamide 55b (0.085 g, 0.33 mmole) and Cs2CO3 (0.1089, 0.33 mmole) in a manner as previously described for example 1. 1H NMR (300 MHz, DMSO-d6) δ 8.50 (1H, d, J=5.5 Hz), 8.12 (1H, s), 7.83 (1H, d, J=8.6 Hz), 7.73 (1H, t, J=5.8 Hz), 7.58 (1H, s), 7.54 (1H, d, J=2.1 Hz), 7.05 (1H, dd, J=2.1, 8.6 Hz), 6.59 (1H, d, J=5.5 Hz), 3.68 (3H, s), 3.17 (2H, t, J=6.1 Hz), 2.61 (3H, s), 1.50 (6H, s), 1.08 (2H, m), 0.43 (2H, m), 0.25 (2H, m); ESIMS (MH+): 533.15.

Sources & evidence

ORD record: ord-e72cc431eab9436ba30e9e21e26522c2
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045528B2

Reaction notes

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