Ammonia → HCID 72205348, compound

HRID 2204373Notes

Reaction equation

HRID 2204373 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:39])=[C:6]([N:8]2[C:15](=[O:16])[C:14]3[CH:13]=[C:12]([C:17]4[CH:18]=[C:19]([CH2:25][C:26]([OH:28])=O)[CH:20]=[CH:21][C:22]=4[O:23][CH3:24])[N:11]([CH:29]([CH3:31])[CH3:30])[C:10]=3[CH:9]2[C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[CH:7]=1.CC[N:42]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.N>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:39])=[C:6]([N:8]2[C:15](=[O:16])[C:14]3[CH:13]=[C:12]([C:17]4[CH:18]=[C:19]([CH2:25][C:26]([NH2:42])=[O:28])[CH:20]=[CH:21][C:22]=4[O:23][CH3:24])[N:11]([CH:29]([CH3:31])[CH3:30])[C:10]=3[CH:9]2[C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[CH:7]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 72204794HCID 72204794, compound

Product 1

HCID 72205348HCID 72205348, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture 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-phenyl}-acetic acid (Example 60) (0.177 mmol), EDC.HCl (0.222 mmol), HOBt (0.131 mmol) and Et3N (0.621 mmol) in CH2Cl2 (1.3 mL) at rt was treated with an ammonia solution (0.4N/THF) (0.52 mmol). After stirring for 16 h, the reaction mixture was diluted with H2O and extracted with CH2Cl2 (2×). The combined organic layers were successively washed with H2O and 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: 7.08 min (HPLC 2); ESI-MS: tR=1.16 min, [M+H]+ 562/564 (LC-MS 1); TLC: Rf=0.14 (EtOAc).

Workup

  1. extractionextracted with CH2Cl2 (2×)
  2. washThe combined organic layers were successively washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-ef41df110a334e9e93cd82af392bd6cf
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

Loading…