Cesium carbonate → HCID 59497804, compound

HRID 1011531Notes

Reaction equation

HRID 1011531 reaction equation
[C:1]([C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[O:36][CH:37]=[CH:38][N:39]=2)=[CH:31][C:30]=1[F:40].ClC1C=CC(S(N(CC2C=CC(C3OC=CN=3)=C(F)C=2F)[C@@H]2CCCC[C@H]2CO)(=O)=O)=CC=1>>[C:1]([C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]1[N:10]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[O:36][CH:37]=[CH:38][N:39]=2)=[CH:31][C:30]=1[F:40])[S:11]([C:14]1[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=1)(=[O:12])=[O:13])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 582017482-(4-(Bromomethyl)-3-fluorophenyl)-1,3-oxazoleHCID 59497774HCID 59497774, compoundHCID 594977804-chloro-N-(2,3-difluoro-4-(oxazol-2-yl)benzyl)-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide

Product 1

HCID 59497804HCID 59497804, compoundYield 70.2%

Procedure

The title compound was synthesized from N-((1R,2R)-2-acetylcyclohexyl)-4-chlorobenzenesulfonamide as a clear oil (550 mg, 1.74 mmol), cesium carbonate (700 mg, 2.15 mmol), and 2-(4-(bromomethyl)-3-fluorophenyl)oxazole (513 mg, 2.00 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 N-((1R,2R)-2-acetylcyclohexyl)-4-chloro-N-(2-fluoro-4-(oxazol-2-yl)benzyl)benzenesulfonamide as a clear oil (600 mg, 70% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.66-7.78 (m, 4H), 7.63 (dd, J=10.83, 1.51 Hz, 1H), 7.51 (t, J=7.93 Hz, 1H), 7.36-7.43 (m, 2H), 7.21 (s, 1H), 4.41 (s, 2H), 3.93 (t, J=10.07 Hz, 1H), 2.74 (1, J=9.57 Hz, 1H), 1.79-1.91 (m, 4H), 1.58-1.71 (m, 3H), 1.43-1.55 (m, 1H), 1.10-1.22 (m, 3H).

Sources & evidence

ORD record
ord-af4973f2e5df4bf9b83594da1f8104a1
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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