Hydrochloric Acid → HCID 89717670, compound

HRID 930191Notes

Reaction equation

HRID 930191 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]2[C:23]3[C:22]4[C:17](=[CH:18][C:19]([C:24]#[N:25])=[CH:20][CH:21]=4)[NH:16][C:15]=3[N:14]=[CH:13][N:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:26]([Sn](CCCC)(CCCC)CCCC)=[N+:27]=[N-:28].Cl.O1CCOCC1>FC(C1C=CC=CC=1)(F)F.C(OCC)C>[N:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]2[C:23]3[C:22]4[C:17](=[CH:18][C:19]([C:24]5[N:26]=[N:27][NH:28][N:25]=5)=[CH:20][CH:21]=4)[NH:16][C:15]=3[N:14]=[CH:13][N:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 4984872Tributyltin azideHCID 89719245HCID 89719245, compound

Product 1

HCID 89717670HCID 89717670, compoundYield 104.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7368(Trifluoromethyl)benzeneSolvent

Conditions

Temperature
180 °C

Procedure

In a 2-5 mL microwave vial was added 4-((3-(piperidin-1-yl)propyl)amino)-9H-pyrimido[4,5-b]indole-7-carbonitrile (47.5 mg, 0.142 mmol) and azidotributyltin (409 μl, 1.491 mmol) in (trifluoromethyl)benzene (2 mL) to give a tan suspension. The vial was placed in the microwave and heated to 180° C. for 30 minutes. The mixture was concentrated to dryness and MeOH (3 mL) followed by HCl 4M in Dioxane (1.07 mL, 4.26 mmol) was added to get a yellow solution. To the resulting solution was added diethyl ether (3 mL) Stirred at 20° C. for 16 hours. The solid obtained was collected on a Buchner. The cake was washed with diethyl ether (3×1 mL) and with Hexane (3×1 mL) and the solid dried at 30° C. under high vacuum until constant weight to afford 56 mg of the title compound as the HCl salt. LCMS m/z 378.2 (M+H)+, retention time (on analytical HPLC)=1.30 minutes.

Workup

  1. customto give a tan suspension
  2. concentrationThe mixture was concentrated to dryness and MeOH (3 mL)
  3. additionwas added
  4. customto get a yellow solution
  5. customThe solid obtained
  6. customwas collected on a Buchner
  7. washThe cake was washed with diethyl ether (3×1 mL) and with Hexane (3×1 mL)
  8. customthe solid dried at 30° C. under high vacuum until constant weight

Sources & evidence

ORD record
ord-709bb6f05546411abb3138be4e120721
Source dataset
uspto-grants-2016_03
Patent number
US09296744B2

Reaction notes

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