Hydrochloric Acid → HCID 58073698, compound

HRID 1916196Notes

Reaction equation

HRID 1916196 reaction equation
Cl[C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:11]=[N:12][C:13]([NH2:16])=[CH:14][CH:15]=2)=[C:6]([CH2:17][CH3:18])[N:5]=[CH:4][N:3]=1.C(OC([N:26]1[CH2:31][CH2:30][C:29]2([CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH2:28][CH2:27]1)=O)(C)(C)C.CCN(C(C)C)C(C)C.Cl>C(#N)C>[CH2:30]1[C:29]2([CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH2:28][CH2:27][N:26]([C:2]2[C:7]([C:8]#[C:9][C:10]3[CH:15]=[CH:14][C:13]([NH2:16])=[N:12][CH:11]=3)=[C:6]([CH2:17][CH3:18])[N:5]=[CH:4][N:3]=2)[CH2:31]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 15296367tert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylateHCID 58073044HCID 58073044, compound

Product 1

HCID 58073698HCID 58073698, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

The title compound is synthesized according to general procedure GP7 (method 2) starting from 1.0 g (3.87 mmol) 4-chloro-6-ethyl-5-(6-amino-pyridin-3-ylethynyl)-pyrimidine and 1.18 g (4.6 mmol) 3,9-diazaspiro[5.5]undecane-3-carboxylic acid tert-butyl ester using 1.97 mL (11.6 mmoL) DIPEA in 20 mL acetonitrile. The reaction mixture is stirred at 80° C. over night. 1.6 ml conc. HCl is added the reaction is stirred for 4 hours at 80° C. The solvent is removed under reduced pressure. The residue is taken up to in acetonitrile and K2CO3 is added. The mixture is stirred at 80° C. over night. The solvent is removed and the residue is taken up in DCM/water. After phase separation the organic phase is extracted twice with DCM. The combined organic layers are dried over Na2SO4, filtered and the solvent is removed under reduced pressure yielding 1.08 g (74%) of crude product, which is used without further purification in the next step.

Workup

  1. stirringis stirred for 4 hours at 80° C
  2. customThe solvent is removed under reduced pressure
  3. additionis added
  4. stirringThe mixture is stirred at 80° C. over night
  5. customThe solvent is removed
  6. customAfter phase separation the organic phase
  7. extractionis extracted twice with DCM
  8. dry with materialThe combined organic layers are dried over Na2SO4
  9. filtrationfiltered
  10. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-c4e37040d55745889ef2a0bc17bcd8d9
Source dataset
uspto-grants-2013_12
Patent number
US08618111B2

Reaction notes

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