N-(3-hydroxypropyl)-4-methylbenzenesulfonamide → 5-isopropyl-N-[6-(3-(4-methylbenzenesulfonylamino)-propoxy)-5-(o-methoxyphenoxy)-2-methyl-4-pyrimidinyl]-2-pyridine sulfonamide

HRID 1358353Notes

Reaction equation

HRID 1358353 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]2[C:19]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][CH3:28])=[C:18](Cl)[N:17]=[C:16]([C:30]3C=CN=CC=3)[N:15]=2)(=[O:12])=[O:11])=[N:8][CH:9]=1)([CH3:3])[CH3:2].[OH:36][CH2:37][CH2:38][CH2:39][NH:40][S:41]([C:44]1[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=1)(=[O:43])=[O:42]>C1COCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]2[C:19]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][CH3:28])=[C:18]([O:36][CH2:37][CH2:38][CH2:39][NH:40][S:41]([C:44]3[CH:45]=[CH:46][C:47]([CH3:50])=[CH:48][CH:49]=3)(=[O:43])=[O:42])[N:17]=[C:16]([CH3:30])[N:15]=2)(=[O:11])=[O:12])=[N:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2180655N-(3-hydroxypropyl)-4-methylbenzenesulfonamideHCID 227294115-isopropyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-4-pyrimidinyl]-2-pyridine sulfonamide

Product 1

HCID 181842255-isopropyl-N-[6-(3-(4-methylbenzenesulfonylamino)-propoxy)-5-(o-methoxyphenoxy)-2-methyl-4-pyrimidinyl]-2-pyridine sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to the procedure described in Example 1a) 256 mg 5-isopropyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-4-pyrimidinyl]-2-pyridine sulfonamide was reacted with N-(3-hydroxy-propyl)-4-methylbenzenesulfonamide in THF in the presence of potassium tert.-butylate to give 280 mg 5-isopropyl-N-[6-(3-(4-methylbenzenesulfonylamino)-propoxy)-5-(o-methoxyphenoxy)-2-methyl-4-pyrimidinyl]-2-pyridine sulfonamide. LC-MS: tR=4.83 min, [M+1]+=705.70, [M−1]−=703.79.

Sources & evidence

ORD record
ord-b8a59f9f72fe41ddbe900e5c1375bd38
Source dataset
uspto-grants-2003_07
Patent number
US06596719B1

Reaction notes

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