Diisopropylethylamine → HCID 11625534, compound

HRID 646883Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[C:20]([C:22]1[O:26][C:25]([C:27](Cl)=[O:28])=[CH:24][CH:23]=1)#[N:21].CCN(C(C)C)C(C)C>>[CH3:12][S:9]([N:8]([CH3:13])[C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:27]([C:25]2[O:26][C:22]([C:20]#[N:21])=[CH:23][CH:24]=2)=[O:28])=[C:3]([N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[CH:4]=1)(=[O:11])=[O:10]

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 202590395-Cyano-2-furoyl chloride

HCID 68679990HCID 68679990, compound

Product 1

HCID 11625534HCID 11625534, compoundYield 23%

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-3457bdb1fb4742e5a38a8ef5f7d0b09f
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705042B2

Reaction notes

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