1H-Imidazole-1-propanamine → HCID 59987457, compound

HRID 658499Notes

Reaction equation

HRID 658499 reaction equation
[F:1][C:2]1([F:35])[O:7][C:6]2[CH:8]=[CH:9][C:10]([NH:12][C:13]([NH:15][C:16]3[CH:32]=[CH:31][C:19]([O:20][C:21]4[CH:26]=[CH:25][N:24]=[C:23]([C:27](OC)=[O:28])[CH:22]=4)=[CH:18][CH:17]=3)=[O:14])=[CH:11][C:5]=2[C:4]([F:34])([F:33])[O:3]1.[Cl-].[Mg+2].[Cl-].[NH2:39][CH2:40][CH2:41][CH2:42][N:43]1[CH:47]=[CH:46][N:45]=[CH:44]1>C1COCC1>[N:43]1([CH2:42][CH2:41][CH2:40][NH:39][C:27]([C:23]2[CH:22]=[C:21]([O:20][C:19]3[CH:18]=[CH:17][C:16]([NH:15][C:13]([NH:12][C:10]4[CH:9]=[CH:8][C:6]5[O:7][C:2]([F:1])([F:35])[O:3][C:4]([F:34])([F:33])[C:5]=5[CH:11]=4)=[O:14])=[CH:32][CH:31]=3)[CH:26]=[CH:25][N:24]=2)=[O:28])[CH:47]=[CH:46][N:45]=[CH:44]1

Participants

5

Reactant 3

HCID 787361H-Imidazole-1-propanamineHCID 5360315Magnesium ChlorideHCID 60125955HCID 60125955, compound

Product 1

HCID 59987457HCID 59987457, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 4-[4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)amino]-carbonyl}amino)phenoxy]pyridine-2-carboxylate (80 mg, 0.16 mmol) and magnesium chloride (16 mg, 0.16 mmol) in THF (2 ml) was added 1-(3-aminopropyl)imidazole (0.04 mL, 0.32 mmol) at room temperature. The reaction mixture was stirred at room temperature for 3 d. The solid was filtered and washed with 10% MeOH in CH2Cl2. The combined filtrate was concentrated to dryness and the residue was purified by column chromatography, eluting with 2 to 5% MeOH/CH2Cl2 to afford 44 mg (45%) of the title compound as a white solid. 1H-NMR (DMSO-d6) δ 9.19 (s, 1H), 9.05 (s, 1H), 8.97 (t, 1H), 8.54 (d, 1H), 8.13 (d, 1H), 7.70-7.58 (m, 4H), 7.42 (d, 1H), 7.38 (d, 1H), 7.19-7.16 (m, 4H), 6.87 (s, 1H), 3.97 (t, 2H), 3.24 (q, 2H), 1.95 (quin, 2H); MS LC-MS(MH)+=587.1, RT=3.14 min.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with 10% MeOH in CH2Cl2
  3. concentrationThe combined filtrate was concentrated to dryness
  4. customthe residue was purified by column chromatography
  5. washeluting with 2 to 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-658e4afb8bdb4f6480e23123e080d99e
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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