1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 58762847, compound

HRID 858038Notes

Reaction equation

HRID 858038 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.[NH2:31][C:32]1[C:33](=[O:48])[N:34]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[F:47])[C:35](=[O:39])[NH:36][C:37]=1[NH2:38]>CN(C)C=O.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16](=[O:18])[NH:31][C:32]2[C:33](=[O:48])[N:34]([CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[F:47])[C:35](=[O:39])[NH:36][C:37]=2[NH2:38])=[CH:13][CH:14]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28249932-(4-((Tert-butoxycarbonyl)amino)phenyl)acetic acidHCID 587628315,6-diamino-3-(2-fluoro-benzyl)-1H-pyrimidine-2,4-dione

Product 1

HCID 58762847HCID 58762847, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (4-tert-butoxycarbonylamino-phenyl)-acetic acid in N,N-dimethylformamide under argon at 25° C. was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The reaction was stirred at 25° C. for 5 min. At this time, the reaction was treated with 5,6-diamino-3-(2-fluoro-benzyl)-1H-pyrimidine-2,4-dione and 4-dimethylarninopyridine. The reaction was stirred at 25° C. for 18 h. At this time, the reaction was concentrated in vacuo. The residue was diluted with water (75 mL) and then acidified to pH=5 with a 1.0N aqueous hydrochloric acid solution. The resulting solid was collected by filtration, rinsed well with water and cold ether, and dried in vacuo to afford (4-{[6-amino-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl]-methyl}-phenyl)-carbamic acid tert-butyl ester (4.10 g, 91%) as a yellow solid; LRMS for C28H32FN5O5 (M+H)+ at m/z=538.

Workup

  1. stirringThe reaction was stirred at 25° C. for 18 h
  2. concentrationAt this time, the reaction was concentrated in vacuo
  3. additionThe residue was diluted with water (75 mL)
  4. filtrationThe resulting solid was collected by filtration
  5. washrinsed well with water and cold ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-adff79f540ff495187fa18d47a10efa3
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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