Triethylamine → HCID 68749168, compound

HRID 1051790Notes

Reaction equation

HRID 1051790 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:11][C@H:12]([C:14]2[N:15]=[C:16]([CH2:25][CH2:26][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][C:18]=3Cl)[CH3:13])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.C(N(CC)CC)C>[Pd].CO>[O:30]1[CH2:29][CH2:28][N:27]([CH2:26][CH2:25][C:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:23]=[C:14]([C@@H:12]([NH:11][C:4]3[C:5]4[N:6]([CH:8]=[CH:9][N:10]=4)[N:7]=[CH:2][CH:3]=3)[CH3:13])[N:15]=2)[CH2:32][CH2:31]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 57330001HCID 57330001, compound

Product 1

HCID 68749168HCID 68749168, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (10%, 10 mg) was added to a mixture of (S)-6-chloro-N-(1-(8-chloro-1-(2-morpholinoethyl)isoquinolin-3-yl)ethyl)imidazo[1,2-b]pyridazin-8-amine 76 (40 mg, 0.085 mmol, 1.0 eq) and triethylamine (0.2 mL, 1.5 mmol, 17.6 eq) in MeOH (10 mL). The resulting mixture was degassed and back-filled with hydrogen three times and then stirred at RT under hydrogen for 5 h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (1-4% MeOH-DCM) to afford the product (S)—N-(1-(1-(2-morpholinoethyl)isoquinolin-3-yl)ethyl)imidazo[1,2-b]pyridazin-8-amine 77. ESI-MS m/z: 403.2 [M+H]+.

Workup

  1. customThe resulting mixture was degassed
  2. additionback-filled with hydrogen three times
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (1-4% MeOH-DCM)

Sources & evidence

ORD record
ord-e23b7bbb27ad4719896023a38306c105
Source dataset
uspto-grants-2016_07
Patent number
US09388183B2

Reaction notes

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