5-cyanofuran-2-carboxylic Acid → HCID 11704205, compound

HRID 646928Notes

Reaction equation

HRID 646928 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]([N+:21]([O-])=O)=[N:10][CH:11]=[C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)[CH:13]=2)[CH2:4][CH2:3]1.[C:24]([C:26]1[O:30][C:29]([C:31](Cl)=[O:32])=[CH:28][CH:27]=1)#[N:25].C(C1OC(C(O)=O)=CC=1)#N>CN(C=O)C>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]([NH:21][C:31]([C:29]3[O:30][C:26]([C:24]#[N:25])=[CH:27][CH:28]=3)=[O:32])=[N:10][CH:11]=[C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)[CH:13]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 108555165-cyanofuran-2-carboxylic AcidHCID 202590395-Cyano-2-furoyl chlorideHCID 58638509HCID 58638509, compound

Product 1

HCID 11704205HCID 11704205, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Methy-5′-(4-methyl-piperazin-1-yl)-2′-nitro-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl (as prepared in the previous step) (319 mg, 1.00 mmol) was converted to corresponding amine according to the procedure in Example 55, step (c) and coupled with 5-cyano-furan-2-carbonyl chloride as prepared in Example 4, step (c) (obtained from 137 mg, 1.00 mmol of 5-cyano-furan-2-carboxylic acid as prepared in Example 1) in DMF (2 mL) at 0° C. The product was isolated by flash chromatography on silica (20% EtOAc/hexane-10% MeOH/EtOAc) to obtain the title compound (16 mg, 4%). 1H-NMR (CDCl3; 400 MHz): δ 9.35 (br s, 1H), 7.95 (br s, 1H), 7.33 (d, 1H, J=3.5 Hz), 7.22 (d, 1H), J=3.5 Hz), 7.06 (br s, 1H), 3.21 (m, 4H), 3.06 (m, 2H), 2.71 (m, 2H), 2.58 (m, 4H), 2.37 (s, 3H), 1.84 (m, 2H), 1.7-1.5 (m, 3H), 1.07 (d, 3H, J=6.3 Hz). LC-MS (ESI, m/z); Calcd. for C22H28N6O2, 409.2 (M+H), found 409.2.

Workup

  1. customThe product was isolated by flash chromatography on silica (20% EtOAc/hexane-10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-484761e49eec4380b4dc3c54d71b7a57
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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