Benzhydrylamine → HCID 57537669, compound

HRID 886628Notes

Reaction equation

Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:9]([OH:13])[C:10]([OH:12])=O)[CH:6]=[N:7][CH:8]=1.[C:14]1([CH:20]([NH2:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C1COCC1.C(OCC)(=O)C>[CH:20]([NH:27][C:10](=[O:12])[CH:9]([C:5]1[CH:6]=[N:7][CH:8]=[C:3]([Br:2])[CH:4]=1)[OH:13])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

(5-Bromo-pyridin-3-yl)-hydroxy-acetic acid HCl salt (1.19 g, 4.47 mmol), C,C-Diphenyl-methylamine (1.3 g, 5.36 mmol), HOAT (2.0 g, 5.36 mmol) and DIEA (1.94 mL, 11.17 mmol) were all combined in THF (43.0 mL) and heated in a closed vial for 20 min. at 60° C. The solution was diluted with ethyl acetate and washed with saturated sodium bicarbonate (1×) and brine (1×). The material was purified by silica gel chromatography using a gradient of hexanes and ethyl acetate (0-100%) to afford N-benzhydryl-2-(5-bromo-pyridin-3-yl)-2-hydroxy-acetamide (1.5 g, 73.5%) as a waxy white solid. MS: m/z 397 (M+H+).

Workup

washwashed with saturated sodium bicarbonate (1×) and brine (1×)
customThe material was purified by silica gel chromatography

Sources & evidence

ORD record: ord-cce1d8e7116b40038e382a6d5e98c15f
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242280B2

Reaction notes

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