Triethylamine → HCID 118390045, compound

HRID 1478091Notes

Reaction equation

HRID 1478091 reaction equation
[Cl:1][C:2]1[C:3]([N:15]([CH3:24])[CH:16]2[CH2:23][CH:19]3[CH2:20][NH:21][CH2:22][CH:18]3[CH2:17]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1.C1C=NC2N([OH:34])N=NC=2C=1.CCN=C=[N:39][CH2:40][CH2:41][CH2:42]N(C)C.CCN(CC)CC>C(Cl)Cl>[Cl:1][C:2]1[C:3]([N:15]([CH3:24])[CH:16]2[CH2:23][CH:19]3[CH2:20][N:21]([C:42](=[O:34])[CH2:41][C:40]#[N:39])[CH2:22][CH:18]3[CH2:17]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 118390026HCID 118390026, compound

Product 1

HCID 118390045HCID 118390045, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-chloro-N4-methyl-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(octahydrocyclopenta[c]pyrrol-5-yl)pyrimidine-2,4-diamine (43.3 mg, 0.51 mmol) in DCM (15 mL) were added HOAT (71.6 mg, 0.53 mmol), EDCI (103.3 mg, 0.53 mmol) and Et3N (111.1 mg, 1.10 mmol). The reaction mixture was stirred at rt for 1 h, then quenched with H2O (30 mL) and extracted with DCM (100 mL×3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/30) to give the title compound as a beige solid (93.1 mg, 91.1%).

Workup

  1. customquenched with H2O (30 mL)
  2. extractionextracted with DCM (100 mL×3)
  3. washThe combined organic phases were washed with brine (100 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/30)

Sources & evidence

ORD record
ord-86c445f95c034d54a6b72eb9f5486831
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

Loading…