Water → HCID 136069598, compound

HRID 2278610Notes

Reaction equation

HRID 2278610 reaction equation
N1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CN(C)[CH2:10][CH2:11][CH2:12][N:13]=[C:14]=NCC.[N:19]1([C:25]2[N:26]=[C:27]([CH2:32][C:33]([O-:35])=O)[NH:28][C:29](=[O:31])[CH:30]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.[Na+].O.[CH3:38]N(C)C=O>C(OCC)(=O)C>[N:19]1([C:25]2[N:26]=[C:27]([CH2:32][C:33](=[O:35])[N:13]3[C:14]4[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:11]4([CH2:10][CH2:38]4)[CH2:12]3)[NH:28][C:29](=[O:31])[CH:30]=2)[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1

Participants

7

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 6228Dimethylformamide2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136069598HCID 136069598, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.14 ml of pyridine and 216 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are successively added to a suspension of 222 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate obtained in the previous step (example 1d, step 2d) in 1 ml of N,N-dimethylformamide. After stirring at ambient temperature for 10 minutes, a solution of 136 mg of 1,2-dihydro-3-spiro-1′-cyclopropyl-1H-indole (which can be prepared according to U.S. Pat. No. 7,507,748 B2 (2009)) in 4 ml of N,N-dimethylformamide is added. The reaction mixture is stirred at ambient temperature for 65 hours, and then 13 ml of water and 26 ml of ethyl acetate are added. After stirring for 1 hour, the precipitate formed is filtered off, and then rinsed successively with water (2×8 ml) and diethyl ether (3×12 ml). After drying under reduced pressure at 40° C., 208 mg of 6-(morpholin-4-yl)-2-[2-oxo-2-(spiro[cyclopropan-1,3′-indol]-1′(2′H)-yl)ethyl]pyrimidin-4(3H)-one are obtained in the form of a pink-colored crystalline powder, the characteristics of which are the following:

Workup

  1. stirringThe reaction mixture is stirred at ambient temperature for 65 hours
  2. stirringAfter stirring for 1 hour
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. washrinsed successively with water (2×8 ml) and diethyl ether (3×12 ml)
  6. customAfter drying under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-1409341d014b4876859814a78215f9fd
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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