Dimethylformamide dimethyl acetal → HCID 178496147, compound

HRID 1405969Notes

Reaction equation

HRID 1405969 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])[C:7]([O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][C:28]2[CH:33]=[C:32]([NH2:34])[C:31]([C:35]#[N:36])=[CH:30][C:29]=2[O:37][CH2:38][CH2:39][O:40][CH3:41])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:42][N:43]([CH:45](OC)OC)[CH3:44]>CCOCC>[C:4]([C:3]1[CH:6]=[C:7]([O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][C:28]2[CH:33]=[C:32](/[N:34]=[CH:42]/[N:43]([CH3:45])[CH3:44])[C:31]([C:35]#[N:36])=[CH:30][C:29]=2[O:37][CH2:38][CH2:39][O:40][CH3:41])[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[CH:9][C:2]=1/[N:1]=[CH:42]/[N:43]([CH3:45])[CH3:44])#[N:5]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 867011962-Amino-5-(2-(2-(2-(2-(5-amino-4-cyano-2-(2-methoxyethoxy)phenoxy)ethoxy)ethoxy)ethoxy)ethoxy)-4-(2-methoxyethoxy)benzonitrile

Product 1

HCID 178496147HCID 178496147, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Amino-5-(2-(2-(2-(2-(5-amino-4-cyano-2-(2-methoxyethoxy)phenoxy)ethoxy)ethoxy)ethoxy)ethoxy)-4-(2-methoxyethoxy)benzonitrile (0.18 g) was added to DMF-DMA (3 mL), the resulting mixture was heated to reflux overnight under N2 atmospheres. After reaction finished, the mixture was diluted with Et2O (30 mL) and solid was collected. The solid was washed with Et2O and air-dried to give (E)-N′-(2-cyano-4-(2-(2-(2-(2-(4-cyano-5-((E)-((dimethylamino)methylene)amino)-2-(2-methoxyethoxy)phenoxy)ethoxy)ethoxy)ethoxy)ethoxy)-5-(2-methoxyethoxy)phenyl)-N,N-dimethylformimidamide (0.2 g) as a yellow solid, which was used in next step directly without any purification.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux overnight under N2 atmospheres
  3. customAfter reaction
  4. customwas collected
  5. washThe solid was washed with Et2O
  6. customair-dried

Sources & evidence

ORD record
ord-f4ff37b0aa8441c7a26223b7971f52e6
Source dataset
uspto-grants-2014_12
Patent number
US08916572B2

Reaction notes

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