Dimethylformamide → HCID 71626459, compound

HRID 1775205Notes

Reaction equation

[CH3:1][C:2]1([CH3:19])[CH2:14][C:13]2=[N:15][NH:16][C:17](=[O:18])[C:10]3[C:11]4[C:12]2=C(NC=4[CH:7]=[CH:8][CH:9]=3)[CH2:3]1.[H-].[Na+].[CH3:22]I.[CH3:24][N:25]([CH:27]=O)[CH3:26]>>[CH3:1][C:2]1([CH3:19])[CH2:14][C:13]2=[N:15][N:16]([CH3:22])[C:17](=[O:18])[C:10]3[C:11]4[C:12]2=[C:27]([N:25]([CH3:24])[C:26]=4[CH:7]=[CH:8][CH:9]=3)[CH2:3]1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 136242904HCID 136242904, compound

Product 1

HCID 71626459HCID 71626459, compoundYield 95%

Procedure

The desired product was prepared using a procedure similar to step 1 of Example 22. Subsequently, 2,2-dimethyl-2,3,5,10-tetrahydro-[1,2]diazepino[3,4,5,6-def]carbazol-6(1H)-one (0.02 g, 0.08 mmol) was reacted with NaH (2.4 mg, 0.1 mmol) and methyl iodide (0.06 g, 0.4 mmol) in DMF (2 ml) to give the desired product (20 mg, 95%) as yellow solid. 1H NMR (DMSO-d6) δ 7.51-7.55 (m, 2H), 7.16 (t, 1H, J=7.8 Hz), 3.69 (s, 3H), 3.42 (s, 3H), 2.72 (s, 2H), 2.27 (s, 2H), and 1.09 (s, 6H). MS (ESI) m/e [M+1]+ 282.

Workup

customThe desired product was prepared

Sources & evidence

ORD record: ord-a749e53cd2894ce293a1c1d8a72cba6a
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260440B2

Reaction notes

Loading…