Diisopropylethylamine → HCID 178453521, compound

HRID 1644233Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:10]=[CH:9]2.[NH2:28][C:29]1[C:30]([C:37]([NH:39][C:40](SC)=[NH:41])=[O:38])=[N:31][C:32]([Cl:36])=[C:33]([NH2:35])[N:34]=1.CCN(C(C)C)C(C)C>CCO>[NH2:28][C:29]1[C:30]([C:37]([NH:39][C:40](=[NH:41])[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[CH:12]=[C:11]([O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])[CH:10]=[CH:9]3)=[O:38])=[N:31][C:32]([Cl:36])=[C:33]([NH2:35])[N:34]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of carbamate 88 (500 mg, 1.34 mmol) and methyl 3,5-diamino-6-chloropyrazine-2-carbonylcarbamimidothioate (10, 790 mg, 2.01 mmol) in EtOH (30 mL) was added DIPEA (1.75 mL, 9.39 mmol) at room temperature. The reaction mixture was heated at 70° C. in a sealed tube for 2 h, then cooled to room temperature, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 90:9:1 CHCl3/CH3OH/NH4OH) to afford carbamate 89 (660 mg, 84%) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ 7.65 (d, J=7.5 Hz, 2H), 7.56 (s, 1H), 7.31 (dd, J=8.4, 1.5 Hz, 1H), 7.16 (d, J=2.4 Hz, 1H), 7.08 (dd, J=8.7, 2.4 Hz, 1H), 4.10 (t, J=6.3 Hz, 2H), 2.81 (t, J=6.6 Hz, 2H), 2.01-1.97 (m, 2H), 1.83-1.60 (m, 4H), 1.43 (s, 9H).

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (silica gel, 90:9:1 CHCl3/CH3OH/NH4OH)

Sources & evidence

ORD record: ord-8afb266f5284470b8195b0b62fd857e5
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124607B2

Reaction notes

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