Ammonium Acetate → HCID 178493441, compound

HRID 1526516Notes

Reaction equation

[CH2:1]([C@:8]1([C:23]([NH:25][CH2:26][C:27]([C:29]2[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([O:37][CH3:38])[CH:30]=2)=O)=O)[O:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:43]>C(O)(=O)C>[CH2:1]([C@:8]1([C:23]2[NH:25][CH:26]=[C:27]([C:29]3[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([O:37][CH3:38])[CH:30]=3)[N:43]=2)[O:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[C:9]1=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To the product from Step B (40 mg, 0.077 mmol) in acetic acid (1 mL) was added ammonium acetate (179 mg, 2.323 mmol) and the mixture heated at 100° C. for 40 h. The solvent was removed and the yellow oil was purified by reverse phase HPLC(YMC Pro-C 18 column, gradient elution, 20% to 90% acetonitrile/water with 0.1% TFA) to afford the title compound as a colorless amorphous solid. LC/MS 498.1 (M+1). IC50 value=B rating

Workup

customThe solvent was removed
customthe yellow oil was purified by reverse phase HPLC(YMC Pro-C 18 column, gradient elution, 20% to 90% acetonitrile/water with 0.1% TFA)

Sources & evidence

ORD record: ord-511f12a8048840cabed3801509dd5c43
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085568B2

Reaction notes

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