Water → HCID 136138825, compound

HRID 2278516Notes

Reaction equation

HRID 2278516 reaction equation
Cl.CN(C)CCCN=C=NCC.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]1[CH2:22][OH:23].[F:24][C:25]1[C:30](=[O:31])[NH:29][C:28]([CH2:32][C:33]([O-])=[O:34])=[N:27][C:26]=1[N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.[Na+].O>CN(C=O)C.N1C=CC=CC=1.ClCCl>[F:24][C:25]1[C:30](=[O:31])[NH:29][C:28]([CH2:32][C:33]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH:14]2[CH2:22][OH:23])=[O:34])=[N:27][C:26]=1[N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1

Participants

8

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27946642,3-dihydro-1H-indol-2-ylmethanolHCID 136069585Sodium (5-fluoro-4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136138825HCID 136138825, compoundYield 42.8%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

471 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 258 mg of (+)-(2,3-dihydro-1H-indol-2-yl)methanol (reference example 8a) are added to a solution of 470 mg of sodium (5-fluoro-4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate in 14 ml of DMF and 14 ml of pyridine. The reaction medium is stirred at ambient temperature for 18 hours then a mixture of water and dichloromethane is added. After settling out, the organic phase is dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue obtained is purified on a silica column, eluent: 95/05 dichloromethane/methanol, so as to give 280 mg of 5-fluoro-2-[2-((−)-2-hydroxymethyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one, the characteristics of which are the following:

Workup

  1. additionis added
  2. dry with materialthe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customis purified on a silica column, eluent

Sources & evidence

ORD record
ord-d7712fda9aab4fc9b17e14f73874c0ba
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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