Dichloromethane → HCID 178492161, compound

HRID 1811878Notes

Reaction equation

HRID 1811878 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][O:9][C:10]1[N:15]=[CH:14][C:13]([NH:16][C:17]2[N:22]=[CH:21][C:20]([CH2:23][N:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]3)=[CH:19][C:18]=2[C:37]2[N:45]=[C:44]([CH3:46])[N:43]=[C:42]3[C:38]=2[N:39]=[CH:40][N:41]3C2CCCCO2)=[CH:12][CH:11]=1.C(Cl)Cl>>[CH3:8][O:9][C:10]1[N:15]=[CH:14][C:13]([NH:16][C:17]2[C:18]([C:37]3[N:45]=[C:44]([CH3:46])[N:43]=[C:42]4[C:38]=3[N:39]=[CH:40][NH:41]4)=[CH:19][C:20]([CH2:23][N:24]3[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]3)=[CH:21][N:22]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66600098tert-butyl 4-((6-(6-methoxypyridin-3-ylamino)-5-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-3-yl)methyl)piperazine-1-carboxylate

Product 1

HCID 178492161HCID 178492161, compound

Procedure

TFA (3.00 mL, 38.9 mmol) was added to a stirred mixture of tert-butyl 4-((6-(6-methoxypyridin-3-ylamino)-5-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-3-yl)methyl)piperazine-1-carboxylate (155 mg, 0.252 mmol) in DCM (3 mL, 46.6 mmol) and the mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated and then diluted with DCM, NaHCO3(aq) and water (10 mL each). The separated aqueous layer was extracted with DCM (3×10 mL) and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give crude N-(6-methoxypyridin-3-yl)-3-(2-methyl-9H-purin-6-yl)-5-(piperazin-1-ylmethyl)pyridin-2-amine

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with DCM, NaHCO3(aq) and water (10 mL each)
  3. extractionThe separated aqueous layer was extracted with DCM (3×10 mL)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-430cecbd68a844d0b1a7423403285fbf
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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