N-Methyl-o-phenylenediamine → HCID 71547301, compound

HRID 1498805Notes

Reaction equation

HRID 1498805 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([CH:15]3[CH2:17][CH:16]3[C:18](O)=O)[CH:9]=2)[N:3]=1.[CH3:21][NH:22][C:23]1[C:28]([NH2:29])=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl.C(N=C=NCCCN(C)C)C.N1C2C(=NC=CC=2)N(O)N=1.C(N(C(C)C)CC)(C)C>O1CCCC1.C(O)(=O)C>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([CH:15]3[CH2:17][CH:16]3[C:18]3[N:22]([CH3:21])[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=4[N:29]=3)[CH:9]=2)[N:3]=1

Participants

8

Reactant 5

HCID 78498N-Methyl-o-phenylenediamineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86732067HCID 86732067, compound

Product 1

HCID 71547301HCID 71547301, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

A slurry of 2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropanecarboxylic acid (2-5, 1.50 g, 5.49 mmol, 1.0 eq.), n-methyl-2-phenylenediamine (1.006 g, 8.23 mmol, 1.0 eq.), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (1.473 g, 7.68 mmol, 1.3 eq.), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (1.046 g, 7.68 mmol) and diisopropylethyl amine (2.88 mL, 16.47 mmol) in tetrahydrofuran (20 mL) was allowed to stir for 16 hours. The solvent was removed by roto-evaporation to afford a dark brown oil. The oil was dissolved in acetic acid (3 mL) and heated at 90° C. for 30 minutes. The solvent was removed by roto-evaporation and the resulting yellow oil was purified by reverse phase liquid chromatography (H2OCH3CN gradient w/ 0.1% NR4OH present) to afford 2-(2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)-1-methyl-1H-benzo[d]imidazole (2-6) as a white powder. 1H NMR (500 MHz, CDCl3) δ 7.69 (m, 2H), 7.28 (m, 3H), 3.82 (s, 3H), 2.90 (s, 3H), 2.83 (m, 2H), 2.68 (s, 3H), 2.41 (s, 3H), 2.19 (m, 2H). HRMS m/z (M+H) 360.1937 found, 360.1931 required.

Workup

  1. customThe solvent was removed by roto-evaporation
  2. customto afford a dark brown oil
  3. customThe solvent was removed by roto-evaporation
  4. customthe resulting yellow oil was purified by reverse phase liquid chromatography (H2OCH3CN gradient w/ 0.1% NR4OH present)

Sources & evidence

ORD record
ord-0f1be931c83b4fbeb57f0cba574215ec
Source dataset
uspto-grants-2015_12
Patent number
US09200001B2

Reaction notes

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