Water → HCID 66584858, compound

HRID 589876Notes

Reaction equation

HRID 589876 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[CH:10]=[N:9][CH2:8][CH2:7][N:6]2[C:11]=1[CH:12]1[CH2:14][CH2:13]1.C([N:17]([CH2:20]C)CC)C.[C:22]([N:26]=[C:27]=[O:28])([CH3:25])([CH3:24])[CH3:23].[OH2:29]>ClCCl>[C:22]([NH:26][C:27]([N:9]1[CH2:8][CH2:7][N:6]2[C:11]([CH:12]3[CH2:14][CH2:13]3)=[C:3]([Br:2])[C:4]([C:20]([NH2:17])=[O:29])=[C:5]2[CH2:10]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 86680817HCID 86680817, compound

Product 1

HCID 66584858HCID 66584858, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5.2 g (16.5 mmol) of 7-bromo-6-cyclopropyl-3,4-dihydropyrrolo[1,2-a]pyrazine hydrochloride and 6.90 ml (49.5 ml) of triethylamine in 200 ml of dichloromethane at 0° C. are added 2.1 ml (18 mmol) of tert-butyl isocyanate. After stirring for 2 hours, 50 ml of water are added and the product is extracted with dichloromethane. The organic phase is separated out, washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on a column of 70 g of silica gel, eluting with a mixture of 5 to 50% ethyl acetate in dichloromethane, to give 4.5 g of N2-tert-butyl-7-bromo-6-cyclopropyl-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide in the form of a white solid after crystallizing from a minimum amount of ethyl acetate, rinsing with diethyl ether and drying.

Workup

  1. extractionthe product is extracted with dichloromethane
  2. customThe organic phase is separated out
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is chromatographed on a column of 70 g of silica gel
  7. washeluting with a mixture of 5 to 50% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-1fca89f448594ebaa66296b96f3635e6
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

Loading…