Phosphorus trichloride → (3aS,6aS)-Ethyl 1-((6-(5-cyano-2-hydroxy-1H-indol-3-yl)pyridin-3-yl)methyl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

HRID 1881339Notes

Reaction equation

HRID 1881339 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([OH:12])=[C:6]2[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:20]2[CH2:24][CH2:23][C@H:22]3[CH2:25][N:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:27][C@@H:21]23)=[CH:15][N+:14]=1[O-])#[N:2].P(Cl)(Cl)Cl>>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([OH:12])=[C:6]2[C:13]1[N:14]=[CH:15][C:16]([CH2:19][N:20]2[CH2:24][CH2:23][C@H:22]3[CH2:25][N:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:27][C@@H:21]23)=[CH:17][CH:18]=1)#[N:2]

Participants

3

Reactant 2

HCID 24387Phosphorus trichlorideHCID 178473354HCID 178473354, compound

Product 1

HCID 136414313(3aS,6aS)-Ethyl 1-((6-(5-cyano-2-hydroxy-1H-indol-3-yl)pyridin-3-yl)methyl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

Procedure

The titled compound was prepared in analogy to example 4.2 starting from 2-(5-cyano-2-hydroxy-1H-indol-3-yl)-5-(((3aS,6aS)-5-(ethoxy-carbonyl)hexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl)methyl)pyridine 1-oxide (100 mg) and phosphorus trichloride (123 mg). The obtained crude product was used without further purification in the next reaction step.

Workup

  1. customThe obtained crude product
  2. customwas used without further purification in the next reaction step

Sources & evidence

ORD record
ord-f836f0a2f3284415a2eeb6b9b08ed583
Source dataset
uspto-grants-2012_11
Patent number
US08318793B2

Reaction notes

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