Morpholine → HCID 53372519, compound

HRID 1753133Notes

Reaction equation

HRID 1753133 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[N:22]([C:23]([C:25]4[C:26]([CH3:30])=[N:27][O:28][CH:29]=4)=[O:24])[CH2:21][CH2:20][N:9]2[C:10](=[O:19])[C:11]2[N:12]([C:14]([CH:17]=O)=[CH:15][CH:16]=2)[CH2:13]3)=[CH:4][CH:3]=1.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[N:22]([C:23]([C:25]4[C:26]([CH3:30])=[N:27][O:28][CH:29]=4)=[O:24])[CH2:21][CH2:20][N:9]2[C:10](=[O:19])[C:11]2[N:12]([C:14]([CH2:17][N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)=[CH:15][CH:16]=2)[CH2:13]3)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 86657084HCID 86657084, compound

Product 1

HCID 53372519HCID 53372519, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

10a-(4-chlorophenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-5-oxo-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazine-8-carbaldehyde (25 mg, 0.059 mmol) and morpholine (10.2 μL) were combined and stirred at room temperature in 1,2-dichloroethane for 10 min. To the mixture was added sodium triacetoxyborohydride (24.7 mg). After 18 h at room temperature the reaction was quenched by the addition of a saturated aqueous solution of NaHCO3 (1 mL) and CH2Cl2 (5 mL). The organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo to give a yellow solid. The solid was purified by flash column chromatography (Biotage SP4, 4 g cartridge, 0-5% MeOH gradient in CH2Cl2) to give 10a-(4-chlorophenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-8-(morpholin-4-ylmethyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (25) as a white solid (26 mg, yield 89%).

Workup

  1. customAfter 18 h at room temperature the reaction was quenched by the addition of a saturated aqueous solution of NaHCO3 (1 mL) and CH2Cl2 (5 mL)
  2. washThe organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a yellow solid
  7. customThe solid was purified by flash column chromatography (Biotage SP4, 4 g cartridge, 0-5% MeOH gradient in CH2Cl2)

Sources & evidence

ORD record
ord-65ab7ae15a6b41bab9ead26f095e8400
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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