Diisopropylethylamine → HCID 178512147, compound

HRID 1696855Notes

Reaction equation

HRID 1696855 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:38])[CH2:9][N:10]([CH2:26][C@H:27]([OH:37])[C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([CH2:35][OH:36])[CH:29]=2)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])=[CH:17][CH:16]=2)=[CH:4][C:3]=1[CH2:39][OH:40].I.[NH2:42][C:43]1[C:44]([C:51]([NH:53][C:54](=[NH:57])SC)=[O:52])=[N:45][C:46]([Cl:50])=[C:47]([NH2:49])[N:48]=1.C(N(C(C)C)CC)(C)C>C(O)C>[OH:37][C@H:27]([C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([CH2:35][OH:36])[CH:29]=1)[CH2:26][N:10]([CH2:9][C@@H:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([CH2:39][OH:40])[CH:4]=1)[OH:38])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:54]([NH:53][C:51]([C:44]2[C:43]([NH2:42])=[N:48][C:47]([NH2:49])=[C:46]([Cl:50])[N:45]=2)=[O:52])=[NH:57])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58100137HCID 58100137, compoundHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

Product 1

HCID 178512147HCID 178512147, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A solution containing 66 (45 mg, 0.08 mmol) dissolved in ethanol (4 mL) was heated to 65° C. The reaction mixture was treated with 1-(3,5-diamino-6-chloropyrazine-2-carbonyl)-2-methylisothiourea hydriodide (32 mg, 0.12 mmol) and diisopropylethylamine (0.40 μL). The reaction mixture was stirred at that temperature for 5 h under N2 atmosphere. The solution was concentrated in vacuo. The resulting residue was first purified by column chromatography eluting with a mixture of 0-20% (10% concentrated ammonium hydroxide in methanol) and dichloromethane and then further purified by preparative TLC using the same solvent system to afford the desired product 67 (18 mg, 30%) as a pale yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 7.26 (s, 1H), 7.10 (s, 2H), 6.97 (s, 1H), 6.68 (s, 1H), 6.58 (s, 1H), 4.88 (br, 1H), 4.46 (s, 3H), 3.16 (s, 2H), 1.58-1.23 (m, 6H); m/z (ESI) 766 [C39H53ClN8O7+H]+.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customThe resulting residue was first purified by column chromatography
  3. washeluting with a mixture of 0-20% (10% concentrated ammonium hydroxide in methanol) and dichloromethane
  4. customfurther purified by preparative TLC

Sources & evidence

ORD record
ord-fa52ef53e37c4638b6410c6400cc1f95
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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