Triethylamine → HCID 69591893, compound

HRID 1827581Notes

Reaction equation

HRID 1827581 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:16][C:17]1[CH:18]=[C:19]([CH:45]=[CH:46][CH:47]=1)[CH2:20][N:21]([S:33]([C:36]1[C:41]([CH3:42])=[CH:40][C:39]([CH3:43])=[CH:38][C:37]=1[CH3:44])(=[O:35])=[O:34])[C:22]1[CH:27]=[CH:26][C:25]([CH:28]=[CH:29][C:30](O)=[O:31])=[CH:24][CH:23]=1.C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C.CN(C1C=CN=CC=1)C>[N:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][NH:1][C:30](=[O:31])[CH:29]=[CH:28][C:25]2[CH:26]=[CH:27][C:22]([N:21]([CH2:20][C:19]3[CH:45]=[CH:46][CH:47]=[C:17]([O:16][CH:11]4[CH2:12][CH2:13][CH2:14][CH2:15][O:10]4)[CH:18]=3)[S:33]([C:36]3[C:41]([CH3:42])=[CH:40][C:39]([CH3:43])=[CH:38][C:37]=3[CH3:44])(=[O:35])=[O:34])=[CH:23][CH:24]=2)=[CH:5][CH:6]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 832754-PyridineethanamineHCID 111923Propylphosphonic anhydrideHCID 516892Sodium BicarbonateHCID 69591877HCID 69591877, compound

Product 1

HCID 69591893HCID 69591893, compoundYield 102.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(2-aminoethyl)pyridine (0.017 g, 0.14 mmol) in 0.3 mL methylene chloride was added to 3-{4-[[3-(tetrahydro-pyran-2-yloxy)-benzyl]-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-acrylic acid (0.050 g, 0.09 mmol). Triethylamine (0.07 mL, 0.50 mmol), 1-propanephosphonic acid cyclic anhydride (0.06 mL of a 50 wt. % solution in ethyl acetate, 0.20 mmol), and catalytic DMAP were added. The reaction mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium bicarbonate was added and the aqueous solution was washed with methylene chloride. The organic layer was separated, PS-trisamine resin (0.050 g) was added, and the mixture was stirred at room temperature for three days. The resin was filtered off and the filtrate was concentrated to afford 0.059 g of the title compound of Step A. MS 640.4 (M+1)+

Workup

  1. washthe aqueous solution was washed with methylene chloride
  2. customThe organic layer was separated
  3. additionPS-trisamine resin (0.050 g) was added
  4. stirringthe mixture was stirred at room temperature for three days
  5. filtrationThe resin was filtered off
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-52eea1d1ed12422795fa7a25aff42349
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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