3-Isocyanatopyridine → HCID 70347305, compound

HRID 1736389Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]=[C:8]=[O:9])[CH:2]=1.[Cl:10][C:11]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][C:12]=1[O:13][C:14]1[C:15]([NH:24][S:25]([C:28]2[CH:37]=[CH:36][C:31]3[O:32][CH2:33][CH2:34][O:35][C:30]=3[CH:29]=2)(=[O:27])=[O:26])=[N:16][CH:17]=[N:18][C:19]=1[O:20][CH2:21][CH2:22][OH:23]>C1(C)C=CC=CC=1>[Cl:10][C:11]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][C:12]=1[O:13][C:14]1[C:19]([O:20][CH2:21][CH2:22][O:23][C:8](=[O:9])[NH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[N:18][CH:17]=[N:16][C:15]=1[NH:24][S:25]([C:28]1[CH:37]=[CH:36][C:31]2[O:32][CH2:33][CH2:34][O:35][C:30]=2[CH:29]=1)(=[O:27])=[O:26]

Participants

Conditions

Temperature: 100 °C

Procedure

57 mg of 3-pyridyl isocyanate were added to 121.5 mg of N-[5-(2-chloro-5-methoxy-phenoxy)-6-(2-hydroxy-ethoxy)-pyrimidin-4-yl]-2,3-dihydro-1,4-benzodioxin-6-sulfonamide dissolved in 1 ml of dry toluene. The reaction mixture was stirred at 100° C. for 1 hour. Then, the solution was added to a silica gel column and it was eluted with EtOAc. There was obtained pyridin-3-ylcarbamic acid 2-[5-(2-chloro-5-methoxy -phenoxy]-6-(2,3-dihydro-1,4-benzodioxin-6-ylsulfonylamino) -pyrimidin-4-yloxy]-ethyl ester, white powder, MS: m/e =630.4 (M+H)+.

Workup

additionThen, the solution was added to a silica gel column and it
washwas eluted with EtOAc

Sources & evidence

ORD record: ord-6954d7ddddda46f8a8bf8a450e503497
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05541186

Reaction notes

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