Cesium carbonate → 4-chloro-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)-N-(4-(oxazol-2-yl)benzyl)benzenesulfonamide

HRID 1011525Notes

Reaction equation

HRID 1011525 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=1.[Cl:39][C:40]1[CH:45]=[CH:44][C:43]([S:46]([N:49]([CH2:58][C:59]2[CH:64]=[CH:63][C:62]([C:65]3[O:66][CH:67]=[CH:68][N:69]=3)=[C:61](F)[C:60]=2F)[C@@H:50]2[CH2:55][CH2:54][CH2:53][CH2:52][C@H:51]2[CH2:56][OH:57])(=[O:48])=[O:47])=[CH:42][CH:41]=1>>[Cl:39][C:40]1[CH:45]=[CH:44][C:43]([S:46]([N:49]([C@@H:50]2[CH2:55][CH2:54][CH2:53][CH2:52][C@H:51]2[CH2:56][OH:57])[CH2:58][C:59]2[CH:60]=[CH:61][C:62]([C:65]3[O:66][CH:67]=[CH:68][N:69]=3)=[CH:63][CH:64]=2)(=[O:48])=[O:47])=[CH:42][CH:41]=1

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 210755772-(4-(Bromomethyl)phenyl)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 594977844-chloro-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)-N-(4-(oxazol-2-yl)benzyl)benzenesulfonamideYield 13%

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)phenyl)oxazole (94 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-((1R,2R)-2-(hydroxymethyl)cyclohexyl)-N-(4-(oxazol-2-yl)benzyl)benzenesulfonamide (21 mg, 13%). 1H NMR (400 MHz, CDCl3) δ ppm 7.98 (d, J=8.31 Hz, 2H), 7.70 (d, J=8.00 Hz, 3H), 7.43-7.51 (m, 4H), 7.23 (s, 1H), 4.73 (d, J=15.11 Hz, 1H), 4.09 (d, J=15.00 Hz, 1H), 3.66-3.81 (m, 2H), 3.07 (t, J=10.83 Hz, 1H), 2.62 (br. s., 1H), 1.62-1.73 (m, 1H), 1.37-1.62 (m, 4H), 1.06-1.28 (m, 2H), 0.81-1.06 (m, 2H). Analytical HPLC R.T.=22.99 min. MS [M+H]+=461. HRMS [M+H]+ calc'd 461.1302, found 461.1283. Chiral LC: R.T.=18.97 min., >98% ee.

Sources & evidence

ORD record
ord-4c50c585c89a482a9fa3adfd9dc26cc9
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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