Benzhydrylamine → HCID 57537669, compound

HRID 1693742Notes

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), diphenylmethylamine (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-814c377511bf425e9dda35dcac84d39f
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158647B2

Reaction notes

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