Triethylamine → HCID 11712597, compound

HRID 499915Notes

Reaction equation

HRID 499915 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[N:13]=[C:14]([C:21]([OH:23])=O)[N:15]([CH2:17][CH:18]3[CH2:20][CH2:19]3)[CH:16]=2)=[O:10])=[C:4]([CH3:24])[CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[N:56]1([CH2:62][CH2:63][CH2:64][NH2:65])[CH2:61][CH2:60][O:59][CH2:58][CH2:57]1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[N:13]=[C:14]([C:21]([NH:65][CH2:64][CH2:63][CH2:62][N:56]3[CH2:61][CH2:60][O:59][CH2:58][CH2:57]3)=[O:23])[N:15]([CH2:17][CH:18]3[CH2:20][CH2:19]3)[CH:16]=2)=[O:10])=[C:4]([CH3:24])[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 61055N-(3-Aminopropyl)morpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59421736HCID 59421736, compound

Product 1

HCID 11712597HCID 11712597, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

34.8 mg (0.1 mmol) of 4-({[(4-chloro-2-methylphenyl)amino]carbonyl}amino)-1-(cyclopropylmethyl)-1H-imidazole-2-carboxylic acid (Example 4A) are dissolved in 0.3 ml of DMF and, after addition of 39.7 mg (0.1 mmol) of HBTU and 10.12 mg (14 μl; 0.1 mmol) of triethylamine, stirred at room temperature for 30 minutes. This solution is added to a solution of 28.8 mg (0.2 mmol) of (3-morpholin-4-ylpropyl)amine in 0.1 ml of DMF and shaken overnight. After filtration, the reaction mixture is purified by preparative HPLC (column: Macherey-Nagel VP 50/21 Nucleodur C18 gravity, 5 μm; flow rate: 25 ml/min; eluent A: acetonitrile, eluent B: water+0.1% conc. aqueous ammonia solution, gradient: 0 min 10% A, 2.00 min 10% A, 6.00 min 90% A, 7.00 min 90% A, 7.10 min 10% A, 8 min 10% A; running time: ca. 10 min per separation; wave length: 220 nm). The correct fractions are evaporated in vacuo.

Workup

  1. stirringshaken overnight
  2. filtrationAfter filtration
  3. customthe reaction mixture is purified by preparative HPLC (column: Macherey-Nagel VP 50/21 Nucleodur C18 gravity, 5 μm; flow rate: 25 ml/min; eluent A: acetonitrile, eluent B: water+0.1% conc. aqueous ammonia solution, gradient: 0 min 10% A, 2.00 min 10% A, 6.00 min 90% A, 7.00 min 90% A, 7.10 min 10% A, 8 min 10% A; running time: ca. 10 min per separation; wave length: 220 nm)
  4. customThe correct fractions are evaporated in vacuo

Sources & evidence

ORD record
ord-8b634d7d53644c5d9b3fe31595e017e3
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

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