Acetic Acid → HCID 86728251, compound

HRID 1776848Notes

Reaction equation

HRID 1776848 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].CC(O)=O.[Br:11][C:12]1[CH:31]=[CH:30][C:15]2[O:16][CH2:17][C:18](=O)[CH2:19][N:20]3[C:28]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[CH:22]=[C:21]3[C:14]=2[CH:13]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[Br:11][C:12]1[CH:31]=[CH:30][C:15]2[O:16][CH2:17][CH:18]([NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])[CH2:19][N:20]3[C:28]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[CH:22]=[C:21]3[C:14]=2[CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 5049666Sodium triacetoxyborohydrideHCID 71295500HCID 71295500, compound

Product 1

HCID 86728251HCID 86728251, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N′,N′-dimethylethane-1,2-diamine (39 mg, 0.440 mmol) and CH3COOH (26 mg, 0.440 mmol) were added to the mixture of 2-bromo-6H-benzo[2,3][1,5]oxazocino[5,4-a]indol-7(8H)-one (100 mg, 0.293 mmol) in 1,2-dichloroethane (2 mL). The mixture was stirred at room temperature for 20 minutes. Then NaBH(OAc)3 (93 mg, 0.440 mmol) was added to the mixture. The mixture was stirred at room temperature for 2 hours. The mixture was then quenched with saturated NaHCO3 (30 mL) and extracted with ethyl acetate (15 mL×3). The organic layer was washed with brine (20 mL), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using p-TLC (dichloromethane:MeOH=1:1) to provide N1-(2-bromo-7,8-dihydro-6H-benzo[2,3][1,5]oxazocino[5,4-a]indol-7-yl)-N2,N2-dimethylethane-1,2-diamine. 1H-NMR (CDCl3, 400 MHz) δ 7.51˜7.56 (m, 2H), 7.42 (s, 1H), 7.29˜7.32 (m, 1H), 7.16˜7.18 (m, 1H), 7.06 (t, J=7.2 Hz, 1H), 6.85 (d, J=8.8 Hz, 1H), 6.56 (s, 1H), 3.86˜4.32 (m, 4H), 2.81˜3.03 (m, 5H), 2.59 (s, 6H). MS (M+H)+: 414/416.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. customThe mixture was then quenched with saturated NaHCO3 (30 mL)
  3. extractionextracted with ethyl acetate (15 mL×3)
  4. washThe organic layer was washed with brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified

Sources & evidence

ORD record
ord-02fc7ad22bb849c4bf26733a00749c46
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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