Sodium Carbonate → HCID 16678949, compound

HRID 1455615Notes

Reaction equation

HRID 1455615 reaction equation
[N:1]1([CH2:10][C:11]([OH:13])=O)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C(N(C(C)C)CC)(C)C.[C:23]1([CH3:35])[CH:28]=[CH:27][CH:26]=[C:25]([C:29]2[CH:33]=[C:32]([NH2:34])[O:31][N:30]=2)[CH:24]=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[N:1]1([CH2:10][C:11]([NH:34][C:32]2[O:31][N:30]=[C:29]([C:25]3[CH:24]=[C:23]([CH3:35])[CH:28]=[CH:27][CH:26]=3)[CH:33]=2)=[O:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 805645Benzoimidazol-1-yl-acetic acidHCID 2733179PyBroPHCID 43991533-(3-methylphenyl)-1,2-oxazol-5-amine

Product 1

HCID 16678949HCID 16678949, compoundYield 1.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1H-Benzimidazol-1-yl)acetic acid (50 mg, 0.28 mmol) (Example 1B) suspended in dichloromethane (5 mL) and diisopropylethylamine (0.19 mL, 1.12 mmol) and stirred for 1 h at room temperature until a clear solution was observed. 3-m-Tolyl-isoxazol-5-yl amine (53 mg, 0.28 mmol) and bromotripyrrolidinophosphonium hexaflurophosphate (PyBroP) (130 mg, 0.28 mmol) were then added and stirred for 24 h at room temperature. Sodium carbonate was then added and the mixture passed through a hydrophobic frit. The organic layer was collected and evaporated to dryness. The residue was then purified by preparative HPLC affording title compound 1 mg. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.34 (3H, s), 5.07 (2H, s), 6.50 (1H, s), 7.17-7.24 (3H, m), 7.33 (1H, t, J=7.6 Hz), 7.52 (2H, t, J=8.6 Hz), 7.57 (1H, s), 7.65 (1H, d, J=7.2 Hz), 8.18 (1H, s). MS (ES) m/z: 333.1 [M+H].

Workup

  1. customThe organic layer was collected
  2. customevaporated to dryness
  3. customThe residue was then purified by preparative HPLC

Sources & evidence

ORD record
ord-e47ffcd28a734988ab076af93958bdb4
Source dataset
uspto-grants-2009_01
Patent number
US07482469B2

Reaction notes

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