Citric Acid → Benzylsulfamic acid [6-chloro-2-(2-cyano-pyridin-4-yl)-5-(2-methoxy-phenoxy) pyrimidin-4-yl]-amide

HRID 1181244Notes

Reaction equation

HRID 1181244 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6](Cl)[N:5]=[C:4]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]#[N:25])[CH:19]=2)[N:3]=1.C(N(C(C)C)C(C)C)C.[K].[CH2:36]([NH:43][S:44](=[O:47])(=[O:46])[NH2:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]#[N:25])[CH:19]=2)[N:5]=[C:6]([NH:45][S:44](=[O:46])(=[O:47])[NH:43][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 81531DiisopropylethylamineHCID 114629344-(4,6-Dichloro-5-(2-methoxyphenoxy)pyrimidin-2-yl)picolinonitrileHCID 68727905Benzylsulfamic acid amide potassium salt

Product 1

HCID 21041243Benzylsulfamic acid [6-chloro-2-(2-cyano-pyridin-4-yl)-5-(2-methoxy-phenoxy) pyrimidin-4-yl]-amideYield 93%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-[4,6-Dichloro-5-(2-methoxy-phenoxy)-pyrimidin-2-yl]-pyridine-2-carbonitrile (3.2 g) was dissolved in DMSO (20 ml), N-ethyldiisopropylamine (1.7 ml) and benzylsulfamic acid amide potassium salt (3.52 g) was added. The mixture was stirred for 18 h at rt, poured onto ice/water, acidified with solid citric acid and the precipitate was filtered off and recrystallized form EtOAc to give benzylsulfamic acid [6-chloro-2-(2-cyano-pyridin-4-yl)-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide (4.17 g). LC-MS: tR=5.55; [M+H]+=523.29.

Workup

  1. additionpoured onto ice/water
  2. filtrationthe precipitate was filtered off
  3. customrecrystallized
  4. customform EtOAc

Sources & evidence

ORD record
ord-f7a2e113fbff4ff9b4fab7a0b8fb0885
Source dataset
uspto-grants-2007_10
Patent number
US07285549B2

Reaction notes

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