Dimethylformamide dimethyl acetal → HCID 178516551, compound

HRID 2205403Notes

Reaction equation

HRID 2205403 reaction equation
C[N:2](C)[CH:3]=[N:4][C:5]([C:7]1[C:12]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][C:10](=[O:20])[N:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:8]=1)=O.O=C1[N:34](C2C=CC=CC=2)C=C(C(N)=O)C(OC2C=CC=CC=2)=C1.COC(OC)N(C)C>>[O:13]([C:12]1[C:7]([C:5]2[N:4]=[CH:3][NH:2][N:34]=2)=[CH:8][N:9]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:10](=[O:20])[CH:11]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 68292229HCID 68292229, compoundHCID 68292617HCID 68292617, compound

Product 1

HCID 178516551HCID 178516551, compoundYield 82%

Conditions

Temperature
120 °C

Procedure

Preparation of N,N-dimethyl-N′-[(6-oxo-4-phenoxy-1-phenyl-1,6-dihydropyridin-3-yl)carbonyl]formamidine: A mixture of 6-oxo-4-phenoxy-1-phenyl-1,6-dihydropyridine-3-carboxamide (195 mg, 0.64 mmol) and N,N-dimethylformamide dimethyl acetal (270 mg, 2.3 mmol) was stirred at 120° C. for 90 min. Then the mixture was cooled down to room temperature and evaporated in vacuo. The residue was crystallized on treatment with Et2O (15 mL). The solid product was filtered and washed with Et2O (2×10 mL) to yield the title compound as beige crystals (190 mg, 82%).

Workup

  1. temperatureThen the mixture was cooled down to room temperature
  2. customevaporated in vacuo
  3. customThe residue was crystallized on treatment with Et2O (15 mL)
  4. filtrationThe solid product was filtered
  5. washwashed with Et2O (2×10 mL)

Sources & evidence

ORD record
ord-213b377d327f4e17bfa338b6021a8288
Source dataset
uspto-grants-2016_06
Patent number
US09371290B2

Reaction notes

Loading…