N,N-Dimethyl-1,3-propanediamine → HCID 69452718, compound

HRID 1375236Notes

Reaction equation

HRID 1375236 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][C:19]([CH3:22])=[N:20][N:21]=2)=[CH:13][C:12]=1[C:23]1[CH:28]=[CH:27][C:26]([C:29]([OH:31])=O)=[CH:25][CH:24]=1.[CH3:32][N:33]([CH3:38])[CH2:34][CH2:35][CH2:36][NH2:37].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH3:32][N:33]([CH2:34][CH2:35][CH2:36][NH:37][C:29]([C:26]1[CH:25]=[CH:24][C:23]([C:12]2[CH:13]=[C:14]([C:17]3[O:18][C:19]([CH3:22])=[N:20][N:21]=3)[CH:15]=[CH:16][C:11]=2[CH3:10])=[CH:28][CH:27]=1)=[O:31])[CH3:38]

Participants

7

Reactant 5

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 112201194-[2-methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]benzoic Acid

Product 1

HCID 69452718HCID 69452718, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIPEA (76 μl, 0.6 mmol) was added to a solution of 2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxylic acid (59 mg, 0.2 mmol), 3-dimethylaminopropylamine (20 mg, 0.2 mmol), HBTU (91 mg, 0.24 mmol) and HOBT (27 mg, 0.2 mmol) in DMF (0.5 ml). The reaction was stirred at room temperature for 16 h. The DMF was evaporated under vacuum and the residue partitioned between DCM (5 ml) and water (5 ml). The organic phase was absorbed onto a silica flash column and eluted with DCM/ethanol/ammonia (80:8:1). The product fractions were concentrated under vacuum to give N-[(dimethylamino)propyl]-2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxamide (37 mg, 49%).

Workup

  1. customThe DMF was evaporated under vacuum
  2. customthe residue partitioned between DCM (5 ml) and water (5 ml)
  3. customThe organic phase was absorbed onto a silica flash column
  4. washeluted with DCM/ethanol/ammonia (80:8:1)
  5. concentrationThe product fractions were concentrated under vacuum

Sources & evidence

ORD record
ord-108c734d698942dc895fba7d8c83a756
Source dataset
uspto-grants-2007_01
Patent number
US07166623B2

Reaction notes

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