HCID 9826559, compound → HCID 66822916, compound

HRID 2401606Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[CH2:17][O:16]2)=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([NH:28][C:29]1([CH3:38])[CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(OC1C=CC([C@H](O)CNC2CC3C(=CC(CC)=C(CC)C=3)C2)=C2C=1NC(=O)C=C2)C1C=CC=CC=1>>[CH2:21]([N:28]([C:29]1([CH3:38])[CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30]1)[CH2:17][C@@H:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([N+:18]([O-:20])=[O:19])[CH:11]=1)[OH:16])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Reactant 3

HCID 9826559HCID 9826559, compound

HCID 10880191(R)-2-(4-(Benzyloxy)-3-nitrophenyl)oxirane

HCID 22499261HCID 22499261, compound

Product 1

HCID 66822916HCID 66822916, compound

Procedure

The title compound is prepared from (R)-2-(4-benzyloxy-3-nitro-phenyl)-oxirane (2.52 g) and benzyl-(2-methyl-indan-2-yl)-amine (2.20 g) by an analogous procedure to that used to prepare (S)-8-Benzyloxy-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxy-ethyl]-1H-quinolin-2-one in Example 19. The reaction is shown to be complete by TLC after 24 hours. The product is purified by flash column chromatography (silica, n-hexane/ethyl acetate 4:1). TLC (silica, n-hexane/ethyl acetate 4:1 Rf=0.30).

Workup

customThe product is purified by flash column chromatography (silica, n-hexane/ethyl acetate 4:1)

Sources & evidence

ORD record: ord-c7410577a4eb45739e0fdc9476013d67
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796307B2

Reaction notes

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