2-Benzyloctahydropyrrolo[3,4-c]pyrrole → HCID 46189672, compound

HRID 1963031Notes

Reaction equation

HRID 1963031 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]3[CH2:13][N:14]([C:17]4[CH:18]=[N:19][C:20](F)=[CH:21][CH:22]=4)[C:15](=[O:16])[C:10]3=[N:9]2)=[CH:4][CH:3]=1.[CH2:24]([N:31]1[CH2:38][CH:37]2[CH:33]([CH2:34][NH:35][CH2:36]2)[CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CS(C)=O>[CH2:24]([N:31]1[CH2:38][CH:37]2[CH2:36][N:35]([C:20]3[N:19]=[CH:18][C:17]([N:14]4[CH2:13][C:11]5[C:10](=[N:9][N:8]([C:5]6[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=6)[CH:12]=5)[C:15]4=[O:16])=[CH:22][CH:21]=3)[CH2:34][CH:33]2[CH2:32]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 44543872-Benzyloctahydropyrrolo[3,4-c]pyrroleHCID 58386124HCID 58386124, compound

Product 1

HCID 46189672HCID 46189672, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of Example 34A (20 mg, 0.061 mmol) in DMSO (0.8 mL) was added 2-benzyloctahydropyrrolo[3,4-c]pyrrole (58 mg, 0.287 mmol). The resulting mixture was irradiated in microwave reactor at 120° C. for 30 min. The sealed tube was heated at 120° C. for 3 h and allowed to cool down to room temperature. The reaction mixture was subjected to filtration. The solid collected was further washed with MeOH (8 mL) and dried under vacuum to give product (16 mg). The obtained product was diluted with CH2Cl2 (0.8 mL) and TFA (0.2 ml). The resulting mixture was stirred at room temperature for 15 min. The solvent was evaporated to give a crude product which was further purified by preparative HPLC (PHENOMENEX® Luna Axia 5μ C18 30×100 mm; 10 min gradient from 70% A: 30% B to 0% A:100% B (A=90% H2O/10% MeOH+0.1% TFA); (13=90% MeOH/10% H2O+0.1% TFA); detection at 220 nm). The desired fraction was collected and concentrated under SPEEDVAC® to give Example 37 as white solid (9.2 mg, 38%). 1H NMR (CD3OD, 400 MHz) δ 3.02-3.90 (m, 10H), 4.47 (s, 2H), 4.94 (s, 2H), 7.09 (d, J=8.8 Hz, 1H), 7.40-7.53 (m, 7H), 7.60-7.80 (m, 2H), 8.25-8.30 (m, 1H), 8.39 (s, 1H), 8.60 (s, 1H). LCMS, [M+H]+=511.4.

Workup

  1. customThe resulting mixture was irradiated in microwave reactor at 120° C. for 30 min
  2. temperatureto cool down to room temperature
  3. filtrationThe reaction mixture was subjected to filtration
  4. customThe solid collected
  5. washwas further washed with MeOH (8 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-6003ee8f32d34fe4847147ad287cd4e6
Source dataset
uspto-grants-2013_04
Patent number
US08415386B2

Reaction notes

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