Cesium carbonate → HCID 25218417, compound

HRID 2061900Notes

Reaction equation

HRID 2061900 reaction equation
[C:1]([O:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][CH:15]2[CH2:17][CH2:16]2)=[C:9](Cl)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH:21]([C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)[NH2:22].C([O-])([O-])=O.[Cs+].[Cs+]>>[C:1]([O:5][C:6]([C:7]1[CH:12]=[CH:11][C:10]2[C:9]([CH:8]=1)=[N:22][N:21]([C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)[C:13]=2[CH2:14][CH:15]1[CH2:17][CH2:16]1)=[O:19])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 223202584-Hydrazinylpyridine hydrochlorideHCID 67212060HCID 67212060, compound

Product 1

HCID 25218417HCID 25218417, compoundYield 42%

Procedure

The reaction was performed according to example 1 using 138.4 mg 3-chloro-4-cyclopropylethynyl-benzoic acid tert-butyl ester, 101.9 mg 4-hydrazinopyridine hydrochloride (1.4 equiv.) and 456.2 mg Cs2CO3 (2.8 equiv.) with a reaction time of 4 hours at 110° C. This afforded 73.0 mg (42%) of the title compound. 1H-NMR (DMSO-d6) δ 0.14-0.18 (m, 2H), 0.40-0.45 (m, 2H), 0.91-1.00 (m, 1H), 1.59 (s, 9H), 3.16 (d, 2H, J=6.8 Hz), 7.54 (dd, 1H, J=8.9, 1.3 Hz), 7.81 (dd, 2H, J=4.5, 1.6 Hz), 7.99 (dd, 1H, J=8.9, 0.8 Hz), 8.85 (dd, 2H, J=4.5, 1.6 Hz); HRMS (FAB): Calculated for C21H24N3O2 (M+H+) 350.1869, found 350.1864.

Sources & evidence

ORD record
ord-e387850e0b7948ba802c42453f3fd026
Source dataset
uspto-grants-2012_10
Patent number
US08283476B2

Reaction notes

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