Diisopropylethylamine → HCID 178514034, compound

HRID 1509864Notes

Reaction equation

Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:21]=[CH:20][C:11]([O:12][CH2:13][CH2:14][NH:15][CH2:16][C:17]([NH2:19])=[O:18])=[CH:10][CH:9]=1.CCN(C(C)C)C(C)C.I.[NH2:32][C:33]1[C:34]([C:41]([NH:43][C:44](=[NH:47])SC)=[O:42])=[N:35][C:36]([Cl:40])=[C:37]([NH2:39])[N:38]=1>C(O)C>[NH2:32][C:33]1[C:34]([C:41]([N:43]=[C:44]([NH2:47])[NH:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]2[CH:21]=[CH:20][C:11]([O:12][CH2:13][CH2:14][NH:15][CH2:16][C:17]([NH2:19])=[O:18])=[CH:10][CH:9]=2)=[O:42])=[N:35][C:36]([Cl:40])=[C:37]([NH2:39])[N:38]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution composed of compound 4 (0.065 g, 0.194 mmol), Hunig's base (0.17 mL, 0.97 mmol) and ethanol (6 mL) was heated at 65° C. for 30 min, then 1-(3,5-diamino-6-chloropyrazine-2-carbony)-2-methylisothiourea hydriodide (5, 0.072 g, 0.213 mmol) was added. The resulting solution was continuously stirred at 65° C. temperature for an additional three hours, then cooled to room temperature. The solvent was then removed by evaporation, and the resulting residue was column chromatographed on silica gel eluting with a mixture of methanol (0-22%), ammonium hydroxide (0-2.2%) and dichloromethane (100-75.8%). This afforded compound 6 (0.078 g, 84%) as a yellow solid. m.p. 92-94° C. (decomposed). 1H NMR (500 MHz, DMSO-d6) δ 1.54 (m, 4H), 2.51 (m, 2H), 2.89 (m, 2H), 3.20 (s, 2H), 3.31 (m, 2H), 4.00 (m, 2H), 6.89 (d, 2H), 7.08 (br, 2H), 7.12 (d, 2H), 7.57 (br, 2H), 9.08 (br, 1H). m/z (ESI) 478.

Workup

temperaturecooled to room temperature
customThe solvent was then removed by evaporation
customchromatographed on silica gel eluting with a mixture of methanol (0-22%), ammonium hydroxide (0-2.2%) and dichloromethane (100-75.8%)

Sources & evidence

ORD record: ord-e4c16e9f706c430d8ee3e1cdacb17c1b
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211895B2

Reaction notes

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