Hydrochloric Acid → HCID 59447034, compound

HRID 1746796Notes

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-b4e1dc9dcad14f5c9ca98a32986359f7
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150519B2

Reaction notes

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