Hydrochloric Acid → HCID 71283257, compound

HRID 1752392Notes

Reaction equation

HRID 1752392 reaction equation
[C:1]([CH:4]1[N:9]([C:10]2[CH:15]=[C:14]([C:16](=[O:18])[NH2:17])[N:13]=[C:12]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)[N:11]=2)[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)(=[O:3])[NH2:2].Cl>O1CCOCC1>[C:1]([CH:4]1[CH2:5][NH:6][CH2:7][CH2:8][N:9]1[C:10]1[N:11]=[C:12]([C:19]2[CH:20]=[CH:21][C:22]([O:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[CH:23][CH:24]=2)[N:13]=[C:14]([C:16]([NH2:17])=[O:18])[CH:15]=1)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71283482HCID 71283482, compound

Product 1

HCID 71283257HCID 71283257, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

As To a milky suspension of the tert-butyl 3-carbamoyl-4-(6-carbamoyl-2-(4-(4-fluorophenoxy)phenyl)pyrimidin-4-yl)piperazine-1-carboxylate (0.363 g, 0.677 mmol) in dioxane (10 mL) was added 4M HCl in dioxane (2 mL, 8 mmol). After stirring for 3 days the reaction was concentrated in vacuo. The solid residue was partitioned between 10 mL EtOAc and 2 mL 2M aqueous Na2CO3 solution. The mixture was diluted with 25 mL EtOAc, 8 mL water and 25 mL brine. The organic layer was separated and the aqueous layer was extracted four times with 25 mL EtOAc. The combined organic layers were dried over MgSO4, filtered, and evaporated in vacuo. The residue was triturated with 2 mL 1:1 EtOAc/hexanes, filtered, and rinsed once with 2 mL 1:1 EtOAc/hexanes. The solid was dried under vacuum at 40° C. to give the product 6-(2-carbamoylpiperazin-1-yl)-2-(4-(4-fluorophenoxy)phenyl)pyrimidine-4-carboxamide as a pale tan powder (0.212 g, 0.486 mmol, 72% yield).

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe solid residue was partitioned between 10 mL EtOAc and 2 mL 2M aqueous Na2CO3 solution
  3. additionThe mixture was diluted with 25 mL EtOAc, 8 mL water and 25 mL brine
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted four times with 25 mL EtOAc
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was triturated with 2 mL 1:1 EtOAc/hexanes
  10. filtrationfiltered
  11. washrinsed once with 2 mL 1:1 EtOAc/hexanes
  12. customThe solid was dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-663e8274843541f2af7ccd3880d263e7
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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