HCID 68681203, compound → HCID 68679990, compound

HRID 646882Notes

Reaction equation

HRID 646882 reaction equation
[CH3:1][N:2]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:8]=1)[S:3]([CH3:6])(=[O:5])=[O:4]>[Pd]>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([N:2]([CH3:1])[S:3]([CH3:6])(=[O:5])=[O:4])=[CH:8][C:9]=1[N:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

3

Reactant 1

HCID 68681203HCID 68681203, compound

Product 1

HCID 68679990HCID 68679990, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Using a procedure similar to Example 23, step (a), N-methyl-N-(4-nitro-3-piperidin-1-yl-phenyl)-methanesulfonamide (89 mg, 0.28 mmol) was stirred with 5% Pd—C (55 mg) under H2 to afford 72 mg (91%) of N-(4-Amino-3-piperidin-1-yl-phenyl)-N-methyl-methanesulfonamide as an oil. Using a procedure similar to Example 4, step (c), N-(4-amino-3-piperidin-1-yl-phenyl)-N-methyl-methanesulfonamide was coupled to 5-cyano-furan-2-carbonyl chloride (77 mg, 0.49 mmol) in the presence of DIEA (107 μL, 0.55 mmol) to afford 26.2 mg (23%) of the title compound as a yellow powder. 1H-NMR (DMSO-d6, 400 MHz): δ 9.66 (s, 1H), 8.10 (d, 1H, J=8.7 Hz), 7.81 (d, 1H, J=3.8 Hz), 7.52 (d, 1H, J=3.7 Hz),), 7.26 (d, 1H, J=2.8 Hz), 7.21-7.19 (m, 1H), 3.23 (s, 3H), 2.95 (s, 3H), 2.84-2.82 (m, 4H), 1.72 (br s, 4H), 1.57 (br s, 2H); Mass spectrum (ESI, m/z): Calcd. for C19H22N4O4S, 403.1 (M+H), found 403.1.

Sources & evidence

ORD record
ord-96b0e104652a4035917b3a5e2eee0c38
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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