Cesium carbonate → HCID 59497783, compound

HRID 1011526Notes

Reaction equation

HRID 1011526 reaction equation
ClC1C=CC(S(N[C@@H]2CCCC[C@H]2CO)(=O)=O)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].BrCC1C=CC(C2OC=CN=2)=CC=1F.[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([S:47]([N:50]([CH2:59][C:60]2[CH:65]=[CH:64][C:63]([C:66]3[O:67][CH:68]=[CH:69][N:70]=3)=[C:62](F)[C:61]=2[F:72])[C@@H:51]2[CH2:56][CH2:55][CH2:54][CH2:53][C@H:52]2[CH2:57][OH:58])(=[O:49])=[O:48])=[CH:43][CH:42]=1>>[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([S:47]([N:50]([CH2:59][C:60]2[CH:65]=[CH:64][C:63]([C:66]3[O:67][CH:68]=[CH:69][N:70]=3)=[CH:62][C:61]=2[F:72])[C@@H:51]2[CH2:56][CH2:55][CH2:54][CH2:53][C@H:52]2[CH2:57][OH:58])(=[O:49])=[O:48])=[CH:43][CH:42]=1

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 582017482-(4-(Bromomethyl)-3-fluorophenyl)-1,3-oxazoleHCID 594977704-chloro-N-(trans-2-hydroxymethylcyclohexyl)benzenesulfonamideHCID 594977804-chloro-N-(2,3-difluoro-4-(oxazol-2-yl)benzyl)-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide

Product 1

HCID 59497783HCID 59497783, compoundYield 14%

Procedure

The title compound was synthesized from 4-chloro-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (100 mg, 0.33 mmol), cesium carbonate (129 mg, 0.40 mmol), and 2-(4-(bromomethyl)-3-fluorophenyl)oxazole (101 mg, 0.40 mmol) according to the procedure described for 4-chloro-N-(2,3-difluoro-4-(oxazol-2-yl)benzyl)-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (Example 20) to give 4-chloro-N-(2-fluoro-4-(oxazol-2-yl)benzyl)-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (22 mg, 14%). 1H NMR (400 MHz, CDCl3) δ ppm 7.63-7.86 (m, 6H), 7.44-7.51 (m, 2H), 7.24 (s, 1H), 4.60 (d, J=15.61 Hz, 1H), 4.38 (d, J=15.00 Hz, 1H), 3.63 (ddd, J=11.83, 4.78, 3.02 Hz, 2H), 3.00-3.11 (m, 1H), 2.57 (br. s., 1H), 1.55-1.70 (m, 3H), 1.43-1.54 (m, 2H), 0.95-1.19 (m, 4H). Analytical HPLC R.T.=23.89 min. MS [M+H]+=479. HRMS [M+H]+ calc'd 479.1208, found 479.1219. Chiral LC: R.T.=9.98 min., >98% ee.

Sources & evidence

ORD record
ord-cf4979ce3b7a4cb3bedc4d999a85dd34
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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