Furfurylamine → HCID 59924871, compound

HRID 2300886Notes

Reaction equation

HRID 2300886 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C@@H:10]([NH:12][C:13]2[N:18]=[C:17]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]=[CH:20]3)[CH:16]=[CH:15][N:14]=2)[CH3:11])[CH:7]=[CH:8][CH:9]=1)(O)=[O:2].[CH2:28]([NH2:34])[C:29]1[O:33][CH:32]=[CH:31][CH:30]=1.Cl.CN(C)CCCN=C=NCC.CN(C1C=CC=CN=1)C>C(Cl)Cl.C(N(CC)CC)C>[O:33]1[CH:32]=[CH:31][CH:30]=[C:29]1[CH2:28][NH:34][C:1]([C:4]1[CH:5]=[C:6]([C@@H:10]([NH:12][C:13]2[N:18]=[C:17]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]=[CH:20]3)[CH:16]=[CH:15][N:14]=2)[CH3:11])[CH:7]=[CH:8][CH:9]=1)=[O:2]

Participants

7

Reactant 4

HCID 3438FurfurylamineHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69962054HCID 69962054, compound

Product 1

HCID 59924871HCID 59924871, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

2-[(S)1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine (EXAMPLE 58, 14.2 mg) and furfurylamine (11 μL, 0.12 mmol) were mixed in CH2Cl2 (2 mL) under nitrogen. Triethylamine (28 μL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (26.3 mg) and dimethylaminopyridine (approx. 1 mg) were added and the mixture stirred at room temperature. After 16 h the mixture was concentrated in vacuo then eluted directly on silica gel (60:40 hexanes:acetone to 50:50 hexanes:acetone) to yield 10.7 mg of the title compound. Mass spectrum (ESI) 439.2 (M+1).

Workup

  1. concentrationAfter 16 h the mixture was concentrated in vacuo
  2. washthen eluted directly on silica gel (60:40 hexanes:acetone to 50:50 hexanes:acetone)

Sources & evidence

ORD record
ord-f496654e378f4c5bae4bef372e232bf2
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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