Dimethylformamide → HCID 20062602, compound

HRID 330544Notes

Reaction equation

HRID 330544 reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][CH3:6].[CH3:7][C:8]1[O:9][CH:10]=[CH:11][C:12]=1[CH2:13][N:14]1[C:18]2=[N:19][CH:20]=[CH:21][CH:22]=[C:17]2[N:16]=[C:15]1[NH:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O>[OH2:4].[OH2:9].[CH2:5]([O:4][CH2:3][CH2:2][N:27]1[CH2:26][CH2:25][CH:24]([NH:23][C:15]2[N:14]([CH2:13][C:12]3[CH:11]=[CH:10][O:9][C:8]=3[CH3:7])[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[N:16]=2)[CH2:29][CH2:28]1)[CH3:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 12341Ethane, 1-chloro-2-ethoxy-HCID 15624007HCID 15624007, compound

Product 1

HCID 20062602HCID 20062602, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.2 parts of 1-chloro-2-ethoxyethane, 3.1 parts of 3-[(2-methyl-3-furanyl)methyl]-N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amine, 1.6 parts of sodium carbonate and 45 parts of N,N-dimethylformamide was stirred overnight at 70° C. The reaction mixture was poured into 50 parts of water. Petroleum ether was added and after stirring, the crystallized product was filtered off, washed with water and petroleum ether and stirred in 1,1'-oxybisethane. The product was filtered off and dried at room temperature, yielding 1.6 parts (38.1%) of N-[1-(2-ethoxyethyl)-4-piperidinyl]-3-[(2-methyl-3-furanyl)methyl]-3H-imidazo-[4,5-b]pyridin-2-amine dihydrate; mp. 84.5° C. (compound 32).

Workup

  1. stirringafter stirring
  2. filtrationthe crystallized product was filtered off
  3. washwashed with water and petroleum ether
  4. stirringstirred in 1,1'-oxybisethane
  5. filtrationThe product was filtered off
  6. customdried at room temperature

Sources & evidence

ORD record
ord-8d73d5a280e1441cac656d66e5a1ac44
Source dataset
uspto-grants-1990_01
Patent number
US04897401

Reaction notes

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