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

HRID 1043492Notes

Reaction equation

HRID 1043492 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-54cf14b150254f218e4f08e3e9f864c8
Source dataset
uspto-grants-2013_10
Patent number
US08563541B2

Reaction notes

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