1,2-Dichloroethane → HCID 86681851, compound

HRID 2276562Notes

Reaction equation

HRID 2276562 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]3[CH2:13][CH2:14][CH2:15][N:16](CCC/C=C/CC(O)=O)[C:10]3=[N:9][C:8]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:5]C=[CH:3][CH:2]=1.[C:32]([NH:39][CH2:40][CH:41]=O)([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].C(O[BH-](O[C:53](=O)[CH3:54])OC(=O)C)(=O)C.[Na+].Cl[CH2:58]CCl>>[C:53]1([CH3:54])[CH:3]=[CH:2][C:1]([C:7]2[N:12]=[C:11]3[CH2:13][CH2:14][CH2:15][N:16]([CH2:41][CH2:40][NH:39][C:32](=[O:33])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[C:10]3=[N:9][C:8]=2[C:26]2[CH:27]=[CH:28][C:29]([CH3:58])=[CH:30][CH:31]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 4247255tert-butyl N-(2-oxoethyl)carbamate2×HCID 5049666Sodium triacetoxyborohydride2×HCID 66665765(E)-7-(2,3-Diphenyl-7,8-dihydropyrido[3,2-b]pyrazin-5(6H)-yl)hept-3-enoic acid2×

Product 1

HCID 86681851HCID 86681851, compound

Procedure

2,3-Dip-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine (Intermediate E) (150 mg, 0.476 mmol) and N-Boc-2-aminoacetaldehyde (151 mg, 0.951 mmol) was suspended in 1,2-dichloroethane (3 ml). After 20 minutes at room temperature, sodium triacetoxyborohydride (252 mg, 1.189 mmol) was added and stirring continued for 2 days at room temperature. A further portion of N-Boc-2-aminoacetaldehyde (100 mg) was added followed by sodium triacetoxyborohydride (252 mg, 1.189 mmol) and the reaction mixture was stirred at room temperature for 3 days. The mixture was partitioned between water and EtOAc and stirring continued for 30 minutes. The organic layer was separated and concentrated in vacuo. The residue was purified by chromatography on silica eluting with 20-60% EtOAc in iso-hexane to afford the title compound;

Workup

  1. waitcontinued for 2 days at room temperature
  2. stirringthe reaction mixture was stirred at room temperature for 3 days
  3. customThe mixture was partitioned between water and EtOAc
  4. stirringstirring
  5. waitcontinued for 30 minutes
  6. customThe organic layer was separated
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica eluting with 20-60% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-a3198eb02ea2464abbe7e0e9a2ddcd40
Source dataset
uspto-grants-2015_09
Patent number
US09132127B2

Reaction notes

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