1,2-Dichloroethane → N-[4-(Hydroxymethyl)-3-pyridinyl]-2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzamide

HRID 1623797Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][OH:9].[C:10]1([CH2:16][O:17][C:18]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)=[CH:23][C:19]=2[C:20](O)=[O:21])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C)C=O.O>[OH:9][CH2:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:1][C:20](=[O:21])[C:19]1[CH:23]=[C:24]([C:27]2[CH:28]=[CH:29][N:30]=[CH:31][CH:32]=2)[CH:25]=[CH:26][C:18]=1[O:17][CH2:16][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 15 °C

Procedure

Neat (3-aminopyridin-4-yl)methanol (may be prepared as described in Description 81; 103 mg, 0.83 mmol) was added in one charge to a stirred suspension of 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79; 180 mg, 0.59 mmol), EDC (226 mg, 1.18 mmol), HOBT (181 mg, 1.179 mmol) and triethylamine (0.16 ml, 1.18 mmol) in N,N-dimethylformamide (1.5 ml) in air at 15° C. The reaction mixture was stirred at 15° C. overnight. 100 ml of water was added. The solid was filtered, and then purified by prep-HPLC (instrument: Gilson-281, Column: Shimadzu 15 um: 250*20 mm*2, Mobile Phase: A: 10 mMol/LNH4HCO3, B: CH3CN, Flow rate: 30.0 ml/L, Gradient: B: 43-55% in 0-7.2 RT=7.5 min, 10.5) to yield the title compound as a white solid. 57 mg.

Workup

filtrationThe solid was filtered
custompurified by prep-HPLC (instrument

Sources & evidence

ORD record: ord-db587f79d4b2416ab18586f2bb81dae5
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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