Benzoic Acid → HCID 18351492, compound

HRID 430895Notes

Reaction equation

[NH2:1][CH2:2]/[CH:3]=[CH:4]/[C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[C:8]#[N:9].[C:20]([OH:28])(=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CN(C(O[N:37]1N=N[C:39]2[CH:40]=[CH:41][CH:42]=C[C:38]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(CC)CC.CN(C=[O:62])C>>[O:62]=[C:38]1[NH:37][CH:42]=[C:41]([C:24]2[CH:23]=[CH:22][C:21]([C:20]([NH:1][CH2:2][CH2:3][CH2:4][C:5]3[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=3[O:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[C:8]#[N:9])=[O:28])=[CH:26][CH:25]=2)[CH:40]=[CH:39]1

Participants

Reactant 5

HCID 243Benzoic Acid

HCID 6228Dimethylformamide

HCID 8471Triethylamine

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

HCID 18351448HCID 18351448, compound

Product 1

HCID 18351492HCID 18351492, compound

Procedure

A solution of (E)-3-(3-aminopropenyl)-4-(2-methoxy-ethoxymethoxy)benzonitrile (0.12 g, 0.46 mmol) in DMF is treated with 6methoxy-pyridin-3-yl)-benzoic acid, TBTU and Et3N as described in EXAMPLE 309, part B. Standard workup and chromatography gives the desired 3-{3-[4-(6-oxo-1,6-dihydro-pyridin-3-yl)benzamido]propyl}-4-(2-methoxyethoxy-methoxy)-benzonitrile (0.22 g, 0.46 mmol). A portion of the benzonitrile (0.09 g, 0.19 mmol) is converted to the benzamidine by treatment with anhydrous HCl/EtOH followed by ammonolysis as described in EXAMPLE 307, part D. The product is purified by HPLC eluting with a gradient of 10% MeCN/H20 (0.1% TFA) to 100% MeCN to give title compound as a white solid (0.05 g, 0.12 mmol). 1H NMR (CD3OD, 300 MHz) δ8.43 (d, 1H), 7.95 (m, 4H), 7.70 (d, 2H), 7.55 (dd, 1H), 6.90 (m, 3H), 6.53 (m, 1H), 4.18 (d, 2H), 3.95 (s, 3H). Ion spray MS [M+1]+=403.

Sources & evidence

ORD record: ord-df050de69c7e4e3a9099007b34a4ba66
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06323227B1

Reaction notes

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