HCID 131728250, compound → HCID 131728249, compound

HRID 2357057Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:46]2[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=2)[O:10][CH:11]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:12]2[O:16][CH:15]([N:17]3[C:25]4[C:20](=[CH:21][C:22]([N+:26]([O-:28])=[O:27])=[CH:23][CH:24]=4)[C:19]([C:29]#[C:30][CH2:31][NH:32]C(=O)C(F)(F)F)=[CH:18]3)[CH2:14][CH:13]2[OH:39])=[CH:5][CH:4]=1>N.CO>[NH2:32][CH2:31][C:30]#[C:29][C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)[N:17]([CH:15]2[O:16][CH:12]([CH:11]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[O:10][CH:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[C:46]3[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=3)[CH:13]([OH:39])[CH2:14]2)[CH:18]=1

Participants

Conditions

Temperature: 8 °C

Procedure

11.0 g (15 mmol) N-[3-(1-{5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-nitro-1H-indol-3-yl)-prop-2-ynyl]-2,2,2-trifluoro-acetamide were dissolved in 260 ml 7N ammonia solution in methanol (Aldrich, 499145). The solution was maintained at 8° C. for 16 h. The solvent was removed in a vacuum on a rotary evaporator (water bath 38° C.). The residue was chromatographed on a silica gel column (Silica gel 60, Merck, 280×85 mm) with a solvent mixture of ethyl acetate:methanol:toluene 1:1:4 (v/v/v) with 0.2 vol % triethylamine (yield: 6.1 g).

Workup

customThe solvent was removed in a vacuum on a rotary evaporator (water bath 38° C.)
customThe residue was chromatographed on a silica gel column (Silica gel 60, Merck, 280×85 mm) with a solvent mixture of ethyl acetate:methanol:toluene 1:1:4 (v/v/v) with 0.2 vol % triethylamine (yield: 6.1 g)

Sources & evidence

ORD record: ord-f87db552fa06484489eb0c097cace3fd
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759469B2

Reaction notes

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