Triethylamine → HCID 72203858, compound

HRID 2204364Notes

Reaction equation

HRID 2204364 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:38])=[C:6]([N:8]2[C:15](=[O:16])[C:14]3[CH:13]=[C:12]([C:17]4[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=4[O:26][CH3:27])[C:20]([OH:22])=O)[N:11]([CH:28]([CH3:30])[CH3:29])[C:10]=3[CH:9]2[C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[CH:7]=1.[CH3:39][S:40]([CH2:43][CH2:44][NH2:45])(=[O:42])=[O:41].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:38])=[C:6]([N:8]2[C:15](=[O:16])[C:14]3[CH:13]=[C:12]([C:17]4[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=4[O:26][CH3:27])[C:20]([NH:45][CH2:44][CH2:43][S:40]([CH3:39])(=[O:42])=[O:41])=[O:22])[N:11]([CH:28]([CH3:30])[CH3:29])[C:10]=3[CH:9]2[C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=2)[CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 43405612-(Methylsulfonyl)ethanamineHCID 72203857HCID 72203857, compound

Product 1

HCID 72203858HCID 72203858, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxy-benzoic acid (Example 35) (0.147 mmol) in DMF (1 mL), were added 2-methanesulfonyl-ethylamine [49773-20-8] (0.183 mmol), EDC.HCl (0.183 mmol), HOBT.H2O (0.109 mmol) and Et3N (0.513 mmol) and the mixture was stirred at rt for 30 h. The mixture was diluted with H2O and extracted with CH2Cl2 (3×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as a white solid. tR: 4.84 min (HPLC 1); ESI-MS: tR=1.19 min, [M+H]+ 654/656/658 (LC-MS 1); TLC: Rf=0.22 (95:5 CH2Cl2/MeOH); 1H-NMR (d6-DMSO, 600 MHz): 8.69 (m, 1H), 7.96 (m, 1H), 7.82 (s, 1H), 7.79 (s, 1H), 7.38 (m, 2H), 7.25 (m, 2H), 7.22 (d, 1H), 7.15 (m, 1H), 7.10 (m, 1H), 6.52 (s, 1H), 6.26 (s, 1H), 3.92 (m, 1H), 3.82 (s, 3H), 3.64 (m, 2H), 3.36 (m, 2H), 3.02 (s, 3H), 1.93 (s, 3H), 1.31 (m, 3H), 0.45 (m, 3H).

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-7a38fc6005a54025bddd4a97c4866eaf
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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