Ethyl orthoformate → HCID 178432043, compound

HRID 2272168Notes

Reaction equation

[NH2:1][C:2]1[CH:14]=[CH:13][C:12]2[C@@H:11]3[C@@H:6]([N:7]([C:15]([C:17]4[CH:25]=[CH:24][C:20]5[NH:21][CH:22]=[N:23][C:19]=5[CH:18]=4)=[O:16])[CH2:8][CH2:9][CH2:10]3)[CH2:5][C:4]=2[C:3]=1[OH:26].C(OCC)(OCC)O[CH2:29][CH3:30]>>[NH:21]1[C:20]2[CH:24]=[CH:25][C:17]([C:15]([N:7]3[C@H:6]4[C@H:11]([C:12]5[CH:4]=[C:3]6[O:26][C:29]([CH3:30])=[N:1][C:2]6=[CH:14][C:13]=5[CH2:5]4)[CH2:10][CH2:9][CH2:8]3)=[O:16])=[CH:18][C:19]=2[N:23]=[CH:22]1

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 178507262HCID 178507262, compound

Product 1

HCID 178432043HCID 178432043, compoundYield 64%

Procedure

(cis-7-Amino-8-hydroxy-2,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridin-1-yl)-(1H-benzoimidazol-5-yl)-methanone (0.10 g) in triethyl orthoformate (0.5 mL) is stirred at 60° C. for 2 h. After cooling to room temperature, the mixture is concentrated and the residue is chromatographed on silica gel (dichloromethane/methanol 1:0→7:3) to afford the title compound. Yield: 64% of theory; LC (method 1): tR=2.28 min; Mass spectrum (ESI+): m/z=373 [M+H]+.

Workup

concentrationthe mixture is concentrated
customthe residue is chromatographed on silica gel (dichloromethane/methanol 1:0→7:3)

Sources & evidence

ORD record: ord-5dbbd6eb9b4b4ece8eaa4541cdc46e25
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120769B2

Reaction notes

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