Aminoacetonitrile hydrochloride → 2-[(4-bromophenyl)(pyridin-2-yl)methoxy]-N-(cyanomethyl)-4-methylpentanamide

HRID 1180393Notes

Reaction equation

[K+].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[O:10][CH:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:12]([O-:14])=O)=[CH:5][CH:4]=1.Cl.[NH2:26][CH2:27][C:28]#[N:29]>>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[O:10][CH:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:12]([NH:29][CH2:28][C:27]#[N:26])=[O:14])=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 11491918Aminoacetonitrile hydrochloride

HCID 69472579HCID 69472579, compound

Product 1

HCID 103197022-[(4-bromophenyl)(pyridin-2-yl)methoxy]-N-(cyanomethyl)-4-methylpentanamide

Procedure

Using the same protocol as described in example 17, step 3, 2-[(4-bromophenyl)(pyridin-2-yl)methoxy]-4-methylpentanoic acid potassium salt from step 3 (662 mg, 1.59 mmol) was coupled with aminoacetonitrile HCl Salt. The crude residue obtained was chromatographed on silica gel using 50% ethyl acetate in hexanes to afford the title compound.

Workup

customThe crude residue obtained
customwas chromatographed on silica gel using 50% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-3725ddcfd1a9418b83f04528bf4d9b59
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279478B2

Reaction notes

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