Aniline → HCID 59924658, compound

HRID 2300777Notes

Reaction equation

HRID 2300777 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)([OH:3])=O.C(N(CC)CC)C.[NH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:36]1([NH:35][C:1]([C:4]2[CH:5]=[C:6]([C@@H:10]([NH:12][C:13]3[N:18]=[C:17]([N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[N:21]=[CH:20]4)[CH:16]=[CH:15][N:14]=3)[CH3:11])[CH:7]=[CH:8][CH:9]=2)=[O:3])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69962054HCID 69962054, compound

Product 1

HCID 59924658HCID 59924658, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine (32.2 mg) was dissolved in CH2Cl2 (2 mL), then triethylamine (62 μL), aniline (25 μL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (62.7 mg) and 4-dimethylaminopyridine (˜1 mg) were added in that order. Mixture stirred 16 h at room temperature then 2 mL more CH2Cl2 added (reaction had gone dry overnight) and thin layer chromatography showed complete conversion of starting material. Concentrated under reduced pressure then purified by silica gel chromatography (98:2 CH2Cl2:MeOH) to yield 16.9 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.48 (br s, 1H); 8.48 (br s, 1H); 8.41 (d, J=5.5 Hz, 1H); 8.00 (s, 1H); 7.75-7.84 (m, 3H); 7.61-7.66 (m, 3H); 7.51 (t, J=7.8 Hz, 1H); 7.33-7.41 (m, 4H); 7.17 (t, J=7.5 Hz, 1H); 6.81 (d, J=5.5 Hz, 1H); 5.73 (br s, 1H); 5.28 (br s, 1H); 1.68 (d, J=6.8 Hz, 3H). Mass Spectrum (ESI): m/e 435.1 (M+1).

Workup

  1. custom(reaction had gone dry overnight) and thin layer chromatography
  2. concentrationConcentrated under reduced pressure
  3. customthen purified by silica gel chromatography (98:2 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-ddb0633c33004132829d843a3d612b84
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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