N,N-Dimethyl-1,3-propanediamine → HCID 25174781, compound

HRID 1097313Notes

Reaction equation

HRID 1097313 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[N:17]4[N:18]=[CH:19][C:20]([C:22]5[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=5)[C:25](O)=[O:26])=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:31][N:32]([CH3:37])[CH2:33][CH2:34][CH2:35][NH2:36].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl.CCOC(C)=O.O>[CH3:31][N:32]([CH3:37])[CH2:33][CH2:34][CH2:35][NH:36][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][CH:30]=[C:22]([C:20]2[CH:19]=[N:18][N:17]3[C:13]([C:11]4[CH:10]=[CH:9][N:8]=[C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[CH:12]=4)=[CH:14][N:15]=[C:16]3[CH:21]=2)[CH:23]=1

Participants

8

Reactant 4

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59443498HCID 59443498, compound

Product 1

HCID 25174781HCID 25174781, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[3-(2-Phenyl-pyridin-4-yl)-imidazo[1,2-b]pyridazin-7-yl]-benzoic acid (Ex. 52) (1 eq, 0.127 mmol, 50 mg), 3-dimethylamino-1-propylamine (3.0 eq, 0.38 mmol, 0.049 ml) and triethylamine (1.30 eq, 0.165, 0.023 ml) are dissolved in DCM (2 ml) and BOP (1.30 eq, 0.165 mmol, 73 mg) is added and the reaction mixture is stirred at room temperature for 20 h. At the completion of this time water and EtOAc are added. The organic phase is separated and the aqueous phase is extracted with EtOAc. The combined organic phases are washed with brine, dried over MgSO4, filtered and the solvent is removed in vacuo. The reaction mixture is purified by flash column chromatography eluting with 9:1 DCM/MeOH to afford N-(3-dimethylamino-propyl)-3-[3-(2-phenyl-pyridin-4-yl)-imidazo[1,2-b]pyridazin-7-yl]-benzamide as a light yellow solid; [M+H]+=477

Workup

  1. customThe organic phase is separated
  2. extractionthe aqueous phase is extracted with EtOAc
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customThe reaction mixture is purified by flash column chromatography
  8. washeluting with 9:1 DCM/MeOH

Sources & evidence

ORD record
ord-2c83839e1e19456697d5c1a9d71c7c47
Source dataset
uspto-grants-2012_03
Patent number
US08143253B2

Reaction notes

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