Diisopropylamine → HCID 136378690, compound

HRID 2278589Notes

Reaction equation

HRID 2278589 reaction equation
Cl.CN(C)CCCN=C=NCC.C(NC(C)C)(C)C.Cl.[NH:21]1[C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([C:30]#[N:31])[C:24]=2[CH2:23][CH2:22]1.[N:32]1([C:38]2[N:39]=[C:40]([CH2:45][C:46]([O-])=[O:47])[NH:41][C:42](=[O:44])[CH:43]=2)[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.[Na+]>CN(C)C=O>[N:32]1([C:38]2[N:39]=[C:40]([CH2:45][C:46]([N:21]3[C:29]4[CH:28]=[CH:27][CH:26]=[C:25]([C:30]#[N:31])[C:24]=4[CH2:23][CH2:22]3)=[O:47])[NH:41][C:42](=[O:44])[CH:43]=2)[CH2:33][CH2:34][O:35][CH2:36][CH2:37]1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53407998HCID 53407998, compoundHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136378690HCID 136378690, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

242 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride, 371 mg of N,N-diisopropylamine and 210 mg of 2,3-dihydro-1H-indole-4-carbonitrile hydrochloride are added to a solution of 300 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate, obtained according to example 1c, step 2c, in 3 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 72 hours and then concentrated under reduced pressure. The residue is taken up with 100 ml of water and 20 ml of ethyl acetate, and then stirred at ambient temperature for 1 hour. The precipitate formed is filtered off, and then rinsed successively with water and petroleum ether. The solid obtained is dried with suction, and then dried under reduced pressure at 40° C. 190 mg of 1-{[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetyl}-2,3-dihydro-1H-indole-4-carbonitrile are thus obtained in the form of a white solid, the characteristics of which are the following:

Workup

  1. customobtained
  2. concentrationconcentrated under reduced pressure
  3. stirringstirred at ambient temperature for 1 hour
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washrinsed successively with water and petroleum ether
  7. customThe solid obtained
  8. customis dried with suction
  9. customdried under reduced pressure at 40° C

Sources & evidence

ORD record
ord-09b1fa423e3c466aaaefc2b8a8b11f0b
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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