3-Methylhistamine → [3-(4Fluorophenyl)(1H-indazol-5-YL)]-N-[2-(1-methylimidazol-5-YL)ethyl]carboxamide

HRID 1272763Notes

Reaction equation

HRID 1272763 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](Cl)=[O:14])=[CH:10][CH:11]=2)[C:6]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:5]1)(=O)C.[CH3:23][N:24]1[C:28]([CH2:29][CH2:30][NH2:31])=[CH:27][N:26]=[CH:25]1>>[F:22][C:19]1[CH:18]=[CH:17][C:16]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[C:9]([C:13]([NH:31][CH2:30][CH2:29][C:28]4[N:24]([CH3:23])[CH:25]=[N:26][CH:27]=4)=[O:14])[CH:8]=3)[NH:4][N:5]=2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 695203-MethylhistamineHCID 224802271-acetyl-3-(4-fluorophenyl)-1H-indazole-5-carbonyl chloride

Product 1

HCID 20789049[3-(4Fluorophenyl)(1H-indazol-5-YL)]-N-[2-(1-methylimidazol-5-YL)ethyl]carboxamideYield 32%

Procedure

The product was synthesized as described in Example 109 using 1-acetyl-3-(4-fluorophenyl)-1H-indazole-5-carbonyl chloride (142.5 mg, 0.45 mmol) and 3-methylhistamine 100 mg, 0.5 mmol). The product was purified by semipreparative HPLC (20–80% acetonitrile gradient over 30 minutes at 20 mL/min) to yield the title compound (52 mg, 32% yield). 1H NMR (DMSO-d6) δ 8.85 (s, 1H), 8.5 (s, 1H), 8.05 (m, 2H), 7.9 (d, 1H), 7.7 (d, 1H), 7.4 (m, 3H), 3.9 (s, 3H), 3.6 (m, 2H), 3.0 (m, 2H). ES-MS m/z 364 [M+1]+.

Workup

  1. customThe product was synthesized
  2. customThe product was purified by semipreparative HPLC (20–80% acetonitrile gradient over 30 minutes at 20 mL/min)

Sources & evidence

ORD record
ord-2b39f30c8cc149df97914d078a0220b2
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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