Sodium Hydroxide → HCID 59807134, compound

HRID 1922396Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 1 M LiAlH4 in THF (1.82 mL, 1.82 mmol) was cooled to 0° C. then treated with 7-amino-1-(2-(dimethylamino)ethyl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (225 mg, 0.91 mmol) (see experimental procedure for the synthesis of Example 25) in 10 mL THF dropwise. The suspension was stirred at room temperature overnight. After this time, the mixture was cooled to 0° C. and treated with 1 mL 1N NaOH dropwise with rapid stirring. After stirring for 20 minutes, the suspension was treated with Na2SO4. The suspension was filtered and the solid was rinsed with 50 mL 10% 2M NH3 in MeOH/CH2Cl2. The filtrate was concentrated and the dark residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2 to give a dark viscous oil (75 mg, 35.4%). 1H-NMR (CDCl3) δ 6.80-6.78 (m, 1H), 6.52-6.48 (m, 2H), 3.40 (brs, 2H), 3.21-3.17 (m, 2H), 2.87-2.83 (m, 2H), 2.70-2.66 (m, 2H), 2.47-2.43 (m, 2H), 2.27 (s, 6H), 1.72-1.64 (m, 2H), 1.59-1.55 (m, 2H). MS (EI): 234.2 (M+1).

Workup

temperatureAfter this time, the mixture was cooled to 0° C.
stirringAfter stirring for 20 minutes
filtrationThe suspension was filtered
washthe solid was rinsed with 50 mL 10% 2M NH3 in MeOH/CH2Cl2
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-cb9b1db1b0ca4ee0bb3d8ddcf4cfd8c0
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173813B2

Reaction notes

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