Hydrochloric Acid → HCID 59447034, compound

HRID 1946818Notes

Reaction equation

[CH:1]1([N:7]([CH2:34][CH:35]2[CH2:37][CH2:36]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:16][C:17]3[CH:33]=[CH:32][C:20]([CH2:21][S:22]([CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])(=[O:24])=[O:23])=[CH:19][CH:18]=3)=[O:15])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>C1COCC1>[CH:1]1([N:7]([CH2:34][CH:35]2[CH2:36][CH2:37]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:16][C:17]3[CH:33]=[CH:32][C:20]([CH2:21][S:22]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])(=[O:24])=[O:23])=[CH:19][CH:18]=3)=[O:15])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of ethyl 3-({4-[({6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]benzyl}sulfonyl)propanoate (Example 130, 130 mg; 0.25 mmol) in THF (5 ml) was treated with concentrated HCl (4 ml). After stirring at RT for 24 hours and 45° C. for 24 hours, the solvent was reduced in vacuo to half the volume and the mixture extracted with EtOAc. The combined organic extracts were washed with water, passed through a hydrophobic frit and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with DCM containing increasing amounts of methanol to give the title compound as a white solid (75 mg, 77%).

Workup

extractionthe mixture extracted with EtOAc
washThe combined organic extracts were washed with water
customthe solvent removed in vacuo
customThe residue was purified by column chromatography (silica)
washeluting with DCM containing
temperatureincreasing amounts of methanol

Sources & evidence

ORD record: ord-28c7b020036547adabe65a016e80a14d
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399448B2

Reaction notes

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