Methylamine → HCID 18387456, compound

HRID 2296748Notes

Reaction equation

CS([CH2:5][CH2:6][CH:7]1[CH:13]=[CH:12][N:11]([C:14](=[O:31])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[CH:17][CH:16]=2)[C:10]2[CH:32]=[CH:33][CH:34]=[CH:35][C:9]=2[S:8]1)(=O)=O.[CH3:36][NH2:37]>O1CCCC1>[CH3:36][NH:37][CH2:5][CH2:6][CH:7]1[CH:13]=[CH:12][N:11]([C:14](=[O:31])[C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[CH:19][CH:20]=2)[C:10]2[CH:32]=[CH:33][CH:34]=[CH:35][C:9]=2[S:8]1

Participants

Conditions

Temperature: 80 °C

Procedure

Compound 13 as prepared in Example 10 (0.045 g, 0.08 mM) and methylamine (40% solution in water; 1 ml) in tetrahydrofuran (4 ml) was heated in a sealed tube with stirring in an 80° C. oil bath for 16 hours. The mixture was cooled to room temperature, evaporated to dryness, diluted with water (30 ml) and extracted with ethyl acetate (2×35 ml). The combined ethyl acetate extracts were dried (MgSO4) and evaporated in vacuo to give a crude mixture. Purification by chromatography (EM silica Gel 60; 10% EtOAc in CH2Cl2) gave the product as a white solid. m/z (MH+)460.

Workup

temperaturewas heated in a sealed tube
temperatureThe mixture was cooled to room temperature
customevaporated to dryness
additiondiluted with water (30 ml)
extractionextracted with ethyl acetate (2×35 ml)
dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
customevaporated in vacuo
customto give a crude mixture
customPurification by chromatography (EM silica Gel 60; 10% EtOAc in CH2Cl2)

Sources & evidence

ORD record: ord-d888401127164abbb2a226353867315f
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06489321B1

Reaction notes

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