HCID 67086980, compound → HCID 178508787, compound

HRID 2365480Notes

Reaction equation

HRID 2365480 reaction equation
[NH2:1][C@@H:2]([CH2:18][NH2:19])[CH2:3][CH2:4][CH2:5][C:6]1[CH:17]=[CH:16][C:9]([O:10][CH2:11][C@H:12]([OH:15])[CH2:13][OH:14])=[CH:8][CH:7]=1.[NH2:20][C:21]1[C:22]([C:29]([NH:31][C:32](=N)SC)=[O:30])=[N:23][C:24]([Cl:28])=[C:25]([NH2:27])[N:26]=1>CC(O)C.CS(C)=O>[OH:15][C@H:12]([CH2:13][OH:14])[CH2:11][O:10][C:9]1[CH:16]=[CH:17][C:6]([CH2:5][CH2:4][CH2:3][C@@H:2]2[CH2:18][NH:19]/[C:32](=[N:31]/[C:29]([C:22]3[C:21]([NH2:20])=[N:26][C:25]([NH2:27])=[C:24]([Cl:28])[N:23]=3)=[O:30])/[NH:1]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 67086980HCID 67086980, compound2×HCID 1404443183,5-Diamino-6-chloro-N-[(methylsulfanyl)methanimidoyl]pyrazine-2-carboxamide2×

Product 1

HCID 178508787HCID 178508787, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of (R)-3-[4-((R)-4,5-Diamino-pentyl)-phenoxy]-propane-1,2-diol (Intermediate 0) (32.8 mg, 0.122 mmol) in propan-2-ol (3 ml) is added 1-(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-2-methyl-isothiourea (Intermediate A) (45.8 mg, 0.122 mmol) and the resultant reaction mixture is heated at 90° C. for 18 hours. The reaction is allowed to cool to room temperature and diluted with DMSO (1.5 ml) and purified on a Waters 3000 preparative HPLC system (Microsorb™ C18, Water (0.1% TFA): MeCN). The fractions containing product are passed through a 1 g SCX-2 cartridge which is eluted with 1:1 Water:MeCN (20 ml), MeCN (20 ml) and 7M NH3 in MeOH (20 ml). The ammonia elutions are concentrated in vacuo to afford the title compound; [M+H]+ 464

Workup

  1. customthe resultant reaction mixture
  2. temperatureto cool to room temperature
  3. custompurified on a Waters 3000 preparative HPLC system (Microsorb™ C18, Water (0.1% TFA): MeCN)
  4. additionThe fractions containing product
  5. washis eluted with 1:1 Water
  6. concentrationThe ammonia elutions are concentrated in vacuo

Sources & evidence

ORD record
ord-0f1b6144fa0c4ba7b5a6e10ad92edfe8
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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