Hydrochloric Acid → HCID 178489165, compound

HRID 2204363Notes

Reaction equation

HRID 2204363 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:37])=[C:6]([N:8]2[C:15](=[O:16])[C:14]3[CH:13]=[C:12]([C:17]4[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=4[O:25][CH3:26])[C:20]#[N:21])[N:11]([CH:27]([CH3:29])[CH3:28])[C:10]=3[CH:9]2[C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[CH:7]=1.[N-:38]=[N+:39]=[N-:40].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:37])=[C:6]([N:8]2[C:15](=[O:16])[C:14]3[CH:13]=[C:12]([C:17]4[CH:18]=[C:19]([C:20]5[NH:40][N:39]=[N:38][N:21]=5)[CH:22]=[CH:23][C:24]=4[O:25][CH3:26])[N:11]([CH:27]([CH3:29])[CH3:28])[C:10]=3[CH:9]2[C:30]2[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 722062793-[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-benzonitrile

Product 1

HCID 178489165HCID 178489165, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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-benzonitrile (Example 17) (0.126 mmol), sodium azide (0.534 mmol) and ammonium chloride (0.534 mmol) in DMF (2 mL) was stirred at 120° C. for 36 h. The mixture was cooled to rt and poured onto ice-H2O and acidified with 1N aqueous HCl. The resulting suspension was filtered. The solid was washed with H2O and dried. The residue was purified by SFC to afford the title compound as a white solid. tR: 4.98 min (HPLC 1); ESI-MS: tR=1.25 min, [M+H]+ 573/575 (LC-MS 1); TLC: Rf=0.21 (9:1 CH2Cl2/MeOH); 1H-NMR (d6-DMSO, 600 MHz): (rotamers) 8.14 (d, 1H), 7.96 (s, 1H), 7.80 (s, 1H), 7.35-7.47 (m, 3H), 7.26 (m, 2H), 7.16 (m, 1H), 7.11 (m, 1H), 6.53 (s, 1H), 6.33 (s, 1H), 3.97 (m, 1H), 3.86 (s, 3H), 1.94 (s, 3H), 1.33 (m, 3H), 0.48 (s, 3H).

Workup

  1. additionpoured onto ice-H2O
  2. filtrationThe resulting suspension was filtered
  3. washThe solid was washed with H2O
  4. customdried
  5. customThe residue was purified by SFC

Sources & evidence

ORD record
ord-bea405fe87d04fcabde7f7deeeb5144a
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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