Hydrochloric Acid → US9433622, Dmx-36

HRID 55864Notes

Reaction equation

HRID 55864 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][C:11]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[C:12]([CH:15]=2)[C:13]#[N:14])[CH:5]=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:23]=[N:24][N:25]([CH2:27][CH2:28][OH:29])[CH:26]=1.Cl>O1CCOCC1>[OH:29][CH2:28][CH2:27][N:25]1[CH:26]=[C:22]([NH:21][C:2]2[N:7]=[C:6]([C:8]3[CH:9]=[N:10][C:11]([N:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)=[C:12]([CH:15]=3)[C:13]#[N:14])[CH:5]=[CH:4][N:3]=2)[CH:23]=[N:24]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 284922672-(4-Amino-1H-pyrazol-1-yl)ethanolHCID 90357141HCID 90357141, compound

Product 1

HCID 78322872US9433622, Dmx-36

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
140 °C

Procedure

5-(2-Chloro-pyrimidin-4-yl)-2-pyrrolidin-1-yl-nicotinonitrile (9) (31 mg, 0.108 mmol) and 2-(4-amino-pyrazol-1-yl)-ethanol (32 mg, 0.252 mmol) were dissolved in 1,4-dioxane (1 mL). 4N HCl in 1,4-dioxane (30 μL, 0.120 mmol) was added and the mixture was heated at 140° C. in the microwave (250 W, stirring) for 90 minutes. The solvent was evaporated in vacuo and the residue dissolved in DMSO (1 mL). The crude product was purified twice by reversed phase preparative LC-MS. Fractions containing desired product were combined and the solvents evaporated in vacuo. The title compound was obtained as a yellow solid (3.7 mg, 9%); LCMS, Rt=7.43 min (Method C), m/z 377 (MH+).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in DMSO (1 mL)
  3. customThe crude product was purified twice by reversed phase preparative LC-MS
  4. additionFractions containing desired product
  5. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-b9b79ddf853e4b708f731fbf8da6add9
Source dataset
uspto-grants-2016_09
Patent number
US09433622B2

Reaction notes

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