Diisopropylethylamine → HCID 11567723, compound

HRID 646887Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[N:12][C:11]([NH2:14])=[C:10]([N:15]3[CH2:20][CH2:19][CH:18]([CH3:21])[CH2:17][CH2:16]3)[N:9]=2)[CH2:4][CH2:3]1.[C:22]([C:24]1[O:28][C:27]([C:29](Cl)=[O:30])=[CH:26][CH:25]=1)#[N:23].CCN(C(C)C)C(C)C>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[N:12][C:11]([NH:14][C:29]([C:27]3[O:28][C:24]([C:22]#[N:23])=[CH:25][CH:26]=3)=[O:30])=[C:10]([N:15]3[CH2:16][CH2:17][CH:18]([CH3:21])[CH2:19][CH2:20]3)[N:9]=2)[CH2:6][CH2:7]1

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 202590395-Cyano-2-furoyl chloride

HCID 68681692HCID 68681692, compound

Product 1

HCID 11567723HCID 11567723, compoundYield 25%

Procedure

Using a procedure similar to Example 23, step (a) 4-methyl-6′-(4-methyl-piperidin-1-yl)-5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (37 mg, 0.11 mmol) was stirred with 20 mg 5% Pd—C in 5 mL MeOH under H2 to afford 32 mg (100%) of the title compound as an oil, which was used immediately without further purification. Using a procedure similar to Example 4, step (c), 4-methyl-6′-(4-methyl-piperidin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-ylamine (32 mg, 0.10 mmol)) was allowed to react with 5-cyano-furan-2-carbonyl chloride (44.6 mg, 0.28 mmol) in the presence of DIEA (107 μL, 0.610 mmol) to afford 10 mg (25%) of the title compound as a dark semi-solid. 1H-NMR (CDCl3; 400 MHz): δ 8.29 (s, 1H), 7.57 (s, 1H), 7.32 (d, 1H, J=3.6 Hz), 7.24-7.23 (d, 1H, J=3.6 Hz), 3.60-3.57 (m, 6H), 2.87-2.81 (m, 2H), 2.57-2.54 (m, 4H), 2.39 (s, 3H), 1.77-1.73 (m, 2H), 1.66-1.55 (m, 1H), 1.40-1.32 (m, 2H), 1.02 (d, 3H, J=6.5 Hz); Mass spectrum (ESI, m/z): Calcd. for C21H27N7O2, 410.2 (M+H), found 410.2.

Workup

customwas used immediately without further purification

Sources & evidence

ORD record: ord-d654d08591f746cb9848c1c42dd508d7
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705042B2

Reaction notes

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