HCID 11299037, compound → HCID 10052981, compound

HRID 2219287Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C@@:9]([CH3:16])([CH:11]([O:14][CH3:15])[O:12][CH3:13])[C@@H:8]3[O:17][C@@H:7]3[C:6]=2[CH:18]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][CH2:27][C:28]2[N:29]=[N:30][N:31]([CH3:33])[N:32]=2)=[CH:22][CH:21]=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C@@:9]([CH3:16])([CH:11]([O:14][CH3:15])[O:12][CH3:13])[C@H:8]([OH:17])[C@@H:7]([N:26]([C:23]3[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=3)[CH2:27][C:28]3[N:29]=[N:30][N:31]([CH3:33])[N:32]=3)[C:6]=2[CH:18]=1

Participants

Reactant 2

HCID 11299037HCID 11299037, compound

HCID 86603164HCID 86603164, compound

Product 1

HCID 10052981HCID 10052981, compoundYield 41.4%

Procedure

The same procedure as step 3 of example 1 was accomplished, except for using (2R,3R,4R)-6-bromo-2-methyl-2-dimethoxymethyl-3,4-epoxy-3,4-dihydro-2H-1-benzopyran (232 mg, 0.74 mmol) and N-(4-chlorophenyl)-N-(2-methyl-2H-tetrazol-5-ylmethyl)amine (164 mg, 0.74 mmol). The crude product was purified by silica gel column chromatography (developing solvent-n-hexane:ethyl acetate=3:1), to give desired compound (165 mg, yield: 41%).

Workup

customThe crude product was purified by silica gel column chromatography (developing solvent-n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record: ord-d8db861ab86842f7bd10e7e09d260d37
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414068B2

Reaction notes

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