Isopropylamine → HCID 86690315, compound

HRID 1428665Notes

Reaction equation

HRID 1428665 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[N:10]=2)[N:5]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:4]=1)=O.[CH:37]([NH2:40])([CH3:39])[CH3:38].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH:37]([NH:40][CH2:1][C:3]1[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:9]([C:12]3[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=3)[N:10]=2)[N:5]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:4]=1)([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86690313HCID 86690313, compound2×

Product 1

HCID 86690315HCID 86690315, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Ethyl 7-(7-formyl-2,3-di-p-tolyl-5H-pyrrolo[2,3-b]pyrazin-5-yl)heptanoate (Intermediate C)(50 mg, 0.103 mmol) in DCE (1 ml) was treated with iso-propylamine (0.027 ml, 0.310 mmol) and stirred at RT for 30 minutes. Sodium triacetoxyborohydride (65.7 mg, 0.310 mmol) was added and stirring continued at RT for 16 hours. The mixture was extracted with DCM (30 ml) and the organic extract was washed with water (×2) and concentrated under reduced pressure to afford the titled compound as an orange oil;

Workup

  1. stirringstirring
  2. waitcontinued at RT for 16 hours
  3. extractionThe mixture was extracted with DCM (30 ml)
  4. extractionthe organic extract
  5. washwas washed with water (×2)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e2098182ad443feb951dff1fc11d201
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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