2-Methoxyaniline → HCID 59924726, compound

HRID 2300887Notes

Reaction equation

HRID 2300887 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].[CH3:28][O:29][C:30]1[C:31]([NH2:36])=[CH:32][CH:33]=[CH:34][CH:35]=1.Cl.CN(C)CCCN=C=NCC.CN(C1C=CC=CN=1)C>C(Cl)Cl.C(N(CC)CC)C>[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH:36][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 70002-MethoxyanilineHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69962054HCID 69962054, compound

Product 1

HCID 59924726HCID 59924726, compoundYield 30.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine (EXAMPLE 58, 23.0 mg) and o-anisidine (22 μL, 0.20 mmol) were mixed in CH2Cl2 (2 mL) under nitrogen. Triethylamine (45 μL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (38.5 mg) and dimethylaminopyridine (approx. 1 mg) were added and the mixture stirred at room temperature. After 19 h the mixture was concentrated in vacuo then eluted directly on silica gel (2:1 hexanes:acetone to 1:1 hexanes:acetone) to yield 9.1 mg of the title compound. Mass spectrum (ESI) 465.2 (M+1).

Workup

  1. concentrationAfter 19 h the mixture was concentrated in vacuo
  2. washthen eluted directly on silica gel (2:1 hexanes:acetone to 1:1 hexanes:acetone)

Sources & evidence

ORD record
ord-e58a5d0ffe034b3cb0fa93bf9ed3b65a
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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