Citric Acid → HCID 21041235, compound

HRID 1181243Notes

Reaction equation

[OH:1][CH2:2][CH2:3][O:4][C:5]1[N:10]=[C:9](S(C)(=O)=O)[N:8]=[C:7]([NH:15][S:16](=[O:26])(=[O:25])[NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:6]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35].[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[OH:1][CH2:2][CH2:3][O:4][C:5]1[N:10]=[C:9]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)[N:8]=[C:7]([NH:15][S:16](=[O:26])(=[O:25])[NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:6]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35]

Participants

Conditions

Temperature: 45 °C

Procedure

Benzylsulfamic acid [6-(2-hydroxy-ethoxy)-2-methanesulfonyl-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide (85 mg) were dissolved in THF (2 ml) and morpholine (2 ml) was added. The reaction mixture was stirred at 45° C. for 48 hours, poured onto water, acidified with solid citric acid and extracted with EtOAc (2×). The combined EtOAc layers were washed with 10% citric acid solution and with brine, dried over magnesium sulfate, filtered and the solvent was evaporated. The crude product was purified by chromatography on plates with toluene/EtOAc=1/1 to give benzylsulfamic acid [6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidin-4-yl]-amide (Example 205) (60 mg). LC-MS: tR=4.69; [M+H]+=532.15.

Workup

additionpoured onto water
extractionextracted with EtOAc (2×)
washThe combined EtOAc layers were washed with 10% citric acid solution and with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
customthe solvent was evaporated
customThe crude product was purified by chromatography on plates with toluene/EtOAc=1/1

Sources & evidence

ORD record: ord-9c73027447fe46e1bb0c3025c016f5f9
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285549B2

Reaction notes

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