Dimethylformamide dimethyl acetal → 6-[(Dimethylamino)methylene]-6,11-dihydro-5H-dipyrido[2,3-b: 3',4'-f]azepin-5-one

HRID 75242Notes

Reaction equation

HRID 75242 reaction equation
[N:1]1[C:6]2[NH:7][C:8]3[CH:16]=[CH:15][N:14]=[CH:13][C:9]=3[CH2:10][C:11](=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1.CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>C1COCC1>[CH3:19][N:20]([CH:22]=[C:10]1[C:9]2[CH:13]=[N:14][CH:15]=[CH:16][C:8]=2[NH:7][C:6]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:11]1=[O:12])[CH3:21]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 668868736,11-Dihydro-5H-dipyrido[2,3-b:3',4'-f]azepin-5-one

Product 1

HCID 668865836-[(Dimethylamino)methylene]-6,11-dihydro-5H-dipyrido[2,3-b: 3',4'-f]azepin-5-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6,11-dihydro-5H-dipyrido[2,3-b:3′,4′-f]azepin-5-one (0.440 g, 2.08 mmol, Intermediate D-6) and 1,1-dimethoxy-N,N-dimethylmethanamine (2.49 mL, 18.7 mmol) in THF (30 mL) was stirred for three days under an atmosphere of nitrogen. The mixture was concentrated in vacuo to give the desired product as an orange solid which was used directly for the next step. LC/MS: 267 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-c6ab17dc0ea444e5b02d67d4361be2f6
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Reaction notes

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