Acetic Acid → HCID 59771033, compound

HRID 2219060Notes

Reaction equation

HRID 2219060 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3CC(NC)C[CH2:18][N:13]3[C:14](=[O:17])[C:15]=2[OH:16])=[O:9])=[CH:4][CH:3]=1.[OH:26]N1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C[CH2:49][N:50]([CH:54]([CH3:56])C)[CH:51]([CH3:53])[CH3:52].C(O)(=O)C>ClCCl.O.C(#N)C>[C:54]([N:50]([CH3:49])[CH:51]1[CH2:52][CH2:18][N:13]2[C:14](=[O:17])[C:15]([OH:16])=[C:10]([C:8]([NH:7][CH2:6][C:5]3[CH:24]=[CH:25][C:2]([F:1])=[CH:3][CH:4]=3)=[O:9])[N:11]=[C:12]2[CH2:53]1)(=[O:26])[CH3:56]

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67147606HCID 67147606, compound

Product 1

HCID 59771033HCID 59771033, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of crude N-(4-fluorobenzyl)-3-hydroxy-8-(methylamino)-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxamide, 1-hydroxybenzotriazole (2 eq.), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (2 eq.), DIPEA (1 eq.) and acetic acid (2 eq) in dichloromethane was stirred for 16 h at room temperature. The solvent was removed under vacuum and the product was isolated by prep. RP-HPLC, using water (0.1% TFA) and acetonitrile (0.1% TFA) as eluents (column: C18). After lyophilization the product was obtained as a fluffy white material.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe product was isolated by prep
  3. customAfter lyophilization the product was obtained as a fluffy white material

Sources & evidence

ORD record
ord-b5738f881f974fc2895fd56cd51ec079
Source dataset
uspto-grants-2008_08
Patent number
US07414045B2

Reaction notes

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