Diisopropylethylamine → HCID 178442121, compound

HRID 1696859Notes

Reaction equation

HRID 1696859 reaction equation
C(N(C(C)C)CC)(C)C.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH:24]([NH:26][CH2:27][C@@H:28]([C:30]2[CH:31]=[C:32]([OH:36])[CH:33]=[CH:34][CH:35]=2)[OH:29])[CH3:25])=[CH:17][CH:16]=1.I.[NH2:38][C:39]1[C:40]([C:47]([NH:49][C:50](=[NH:53])SC)=[O:48])=[N:41][C:42]([Cl:46])=[C:43]([NH2:45])[N:44]=1>C(O)C>[NH2:38][C:39]1[C:40]([C:47]([NH:49][C:50](=[NH:53])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][CH:24]([NH:26][CH2:27][C@H:28]([OH:29])[C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=3)[CH3:25])=[CH:19][CH:20]=2)=[O:48])=[N:41][C:42]([Cl:46])=[C:43]([NH2:45])[N:44]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 66860142HCID 66860142, compoundHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

Product 1

HCID 178442121HCID 178442121, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

Diisopropylethylamine (0.45 mL, 2.58 mmol) was added to a mixture of amino alcohol 142 (0.63 g, 1.69 mmol) and 1-(3,5-diamino-6-chloropyrazine-2-carbonyl)-2-methylisothiourea hydriodide (0.66 g, 2.58 mmol) in absolute ethanol (10 mL). The mixture was stirred at 75° C. (oil bath) for 4.5 h. After this time the mixture was cooled to rt and the solvent was removed by rotary evaporation. Purification by column chromatography (silica gel, a gradient of 5:95 to 10:90 methanol/dichloromethane, followed by a gradient of 5:95 to 10:90 (10% concentrated aqueous ammonium hydroxide/methanol)/dichloromethane) and subsequent drying in a 40° C. vacuum oven for 88 h afforded the phenol derivative 143 (0.30 g, 30% yield) as a yellow solid: mp 82-86° C.; 1H NMR (500 MHz, DMSO-d6) δ 0.93 (dd, 3H, J=6.0, 3.5 Hz), 1.21-1.28 (m, 1H), 1.32-1.40 (m, 1H), 1.49-1.60 (m, 6H), 1.75 (s, 1H), 2.49-2.66 (m, 5H), 3.11-3.19 (m, 2H), 4.44-4.48 (m, 1H), 5.17 (br s, 1H), 6.59-6.72 (m, 6H), 7.06-7.11 (m, 5H), 9.09 (br s, 1H); m/z (ESI) 583 [C29H39ClN8O3+H]+.

Workup

  1. temperatureAfter this time the mixture was cooled to rt
  2. customthe solvent was removed by rotary evaporation
  3. customPurification by column chromatography (silica gel
  4. customsubsequent drying in a 40° C. vacuum oven for 88 h

Sources & evidence

ORD record
ord-21e7b86fb20e44e79252d3f1ff279ac8
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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