N,N-Diethyl-1,3-propanediamine → HCID 21078788, compound

HRID 1375237Notes

Reaction equation

HRID 1375237 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](O)=[O:30])=[CH:25][CH:24]=1.[CH2:32]([N:34]([CH2:39][CH3:40])[CH2:35][CH2:36][CH2:37][NH2:38])[CH3:33].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>[CH2:32]([N:34]([CH2:39][CH3:40])[CH2:35][CH2:36][CH2:37][NH:38][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:30])[CH3:33]

Participants

7

Reactant 5

HCID 61011N,N-Diethyl-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 21078788HCID 21078788, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIPEA (130 μl, 1.0 mmol) was added to a solution of 2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxylic acid (100 mg, 0.34 mmol), 3-diethylaminopropylamine (49 mg, 0.37 mmol), HBTU (155 mg, 0.41 mmol) and HOBT (46 mg, 0.34 mmol) in DMF (1.0 ml). The reaction was stirred at room temperature for 66 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 (100:8:1). The product fractions were concentrated under vacuum to give N-[3-(diethylamino)propyl]-2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxamide (88 mg, 64%).

Workup

  1. customThe DMF was evaporated under vacuum
  2. customthe residue partitioned between DCM (5 ml) and water (5 ml) The organic phase
  3. customwas absorbed onto a silica flash column
  4. washeluted with DCM/ethanol/ammonia (100:8:1)
  5. concentrationThe product fractions were concentrated under vacuum

Sources & evidence

ORD record
ord-2cd1894ddc144faf9bb6558d4202d9f8
Source dataset
uspto-grants-2007_01
Patent number
US07166623B2

Reaction notes

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