HCID 86713256, compound → HCID 71006837, compound

HRID 927868Notes

Reaction equation

COC1C=C(OC)C=CC=1C[N:6]([CH2:37][CH2:38][CH2:39][N:40]([CH3:42])[CH3:41])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH:18][C:19]1[C:28]([C:29]([O:31]C(C)(C)C)=[O:30])=[C:27]2[C:22]([CH:23]3[CH2:36][CH:24]3[CH2:25][O:26]2)=[CH:21][CH:20]=1)(=[O:17])=[O:16])=[O:8]>FC(F)(F)C(O)=O>[CH3:42][N:40]([CH3:41])[CH2:39][CH2:38][CH2:37][NH:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH:18][C:19]1[C:28]([C:29]([OH:31])=[O:30])=[C:27]2[C:22]([CH:23]3[CH2:36][CH:24]3[CH2:25][O:26]2)=[CH:21][CH:20]=1)(=[O:17])=[O:16])=[O:8]

Participants

Conditions

Temperature: 30 °C

Procedure

A solution of tert-butyl (1aRS,7bSR)-5-{2-[N-(2,4-dimethoxybenzyl)-N-(3-dimethylamino-propyl)carbamoyl]benzenesulfonylamino}-1,1a,2,7b-tetrahydro-cyclopropa-[c]chromene-4-carboxylate (Intermediate 119, 0.03 g) in trifluoroacetic acid (5 mL) was stirred and heated at 30° C. overnight. The mixture was evaporated to dryness and the residue was purified by HPLC (C18) to give (1aRS,7bSR)-5-[2-(3-dimethylaminopropylcarbamoyl)benzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid (0.013 g) as a white solid.

Workup

customThe mixture was evaporated to dryness
customthe residue was purified by HPLC (C18)

Sources & evidence

ORD record: ord-4eb7acaafdb043ff846a8f0e6b2f4315
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290472B2

Reaction notes

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