Aluminium lithium hydride → HCID 59144134, compound

HRID 424464Notes

Reaction equation

HRID 424464 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C:8]1[CH:9]=[CH:10][C:11]2[N:16]([CH2:17][CH2:18][CH:19]3[CH2:23][CH2:22][CH2:21][N:20]3[CH3:24])[C:15](=O)[CH2:14][O:13][C:12]=2[CH:26]=1>C1COCC1>[CH3:24][N:20]1[CH2:21][CH2:22][CH2:23][CH:19]1[CH2:18][CH2:17][N:16]1[CH2:15][CH2:14][O:13][C:12]2[CH:26]=[C:8]([NH2:7])[CH:9]=[CH:10][C:11]1=2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 591440677-Amino-4-(2-(1-methylpyrrolidin-2-yl)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

Product 1

HCID 59144134HCID 59144134, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiAlH4 (4.21 mL, 4.212 mmol, 1.0 M solution in THF) was treated dropwise with 7-amino-4-(2-(1-methylpyrrolidin-2-yl)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (0.29 g, 1.053 mmol) in dry THF (5 mL) at 0° C. The resulting mixture was brought to room temperature and stirred overnight. The reaction was carefully quenched with the sequential addition of water (0.16 mL), 2 N NaOH solution (0.16 mL), and water (0.16 mL). The reaction was filtered after stirring for 30 minutes at room temperature and washed with CH2Cl2 (3×10 mL). The combined CH2Cl2 layers were evaporated, and the crude material was purified by column chromatography (5:95 (2M NH3 in MeOH):CH2Cl2) to obtain the title compound (0.23 g, 84%) as a syrup. 1H NMR (DMSO-d6) δ 1.28-1.45 (m, 2H), 1.56-1.65 (m, 2H), 1.75-2.10 (m, 4H), 2.18 (s, 3H), 2.88-2.95 (m, 1H), 3.03-3.10 (m, 4H), 4.08 (t, 2H, J=4.8 Hz), 4.36 (s, 2H), 6.00 (d, 1H, J=2.4 Hz), 6.06 (dd, 1H, J=2.4, 8.5 Hz), 6.43 (d, 1H, J=8.4 Hz); ESI-MS (m/z, %): 262 (MH+, 100), 163 (33), 112 (42).

Workup

  1. customwas brought to room temperature
  2. customThe reaction was carefully quenched with the sequential addition of water (0.16 mL), 2 N NaOH solution (0.16 mL), and water (0.16 mL)
  3. filtrationThe reaction was filtered
  4. stirringafter stirring for 30 minutes at room temperature
  5. washwashed with CH2Cl2 (3×10 mL)
  6. customThe combined CH2Cl2 layers were evaporated
  7. customthe crude material was purified by column chromatography (5:95 (2M NH3 in MeOH):CH2Cl2)

Sources & evidence

ORD record
ord-1e28a4d14a1044c79712a25caf5697c0
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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