2-Butynoic acid → HCID 66780586, compound

HRID 1470391Notes

Reaction equation

HRID 1470391 reaction equation
[C:1](O)(=[O:5])[C:2]#[C:3][CH3:4].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)C(C)C)(C)C.[O:31]([C:38]1[CH:60]=[CH:59][C:41]([O:42][C:43]2[CH:48]=[CH:47][N:46]=[C:45]3[CH:49]=[C:50]([C:52]4[CH:53]=[C:54]([CH:56]=[CH:57][CH:58]=4)[NH2:55])[O:51][C:44]=23)=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O1CCOCC1>[O:31]([C:38]1[CH:60]=[CH:59][C:41]([O:42][C:43]2[CH:48]=[CH:47][N:46]=[C:45]3[CH:49]=[C:50]([C:52]4[CH:53]=[C:54]([NH:55][C:1](=[O:5])[C:2]#[C:3][CH3:4])[CH:56]=[CH:57][CH:58]=4)[O:51][C:44]=23)=[CH:40][CH:39]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 685352-Butynoic acidHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 56848930HCID 56848930, compound

Product 1

HCID 66780586HCID 66780586, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 20-mL glass vial was added but-2-ynoic acid (7.57 mg; 0.09 mmol), and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (28.66 mg; 0.11 mmol), and N,N-diisopropylethylamine (0.05 ml; 0.30 mmol) suspended in dioxane (3.00 ml). The reaction mixture was stirred at room temperature for 1 hour. 3-[7-(4-phenoxyphenoxy)furo[3,2-b]pyridin-2-yl]aniline (29.60 mg; 0.08 mmol.) was added. The reaction mixture was then stirred at room temperature overnight. The mixture was purified using preparative HPLC to afford the title compound as a white solid (30.00 mg, 87%). HPLC (method F): 100%, RT=4.400 min. 1H NMR (DMSO-d6) δ [ppm] 10.79 (s, 1H), 8.40 (d, 1H), 8.24 (s, 1H), 7.70 (d, 1H), 7.66 (d, 1H), 7.62 (s, 1H), 7.47 (t, 1H), 7.41 (t, 2H), 7.38 (d, 2H), 7.16 (m, 3H), 7.08 (d, 2H), 6.77 (d, 1H), 2.05 (s, 3H). MS: m/z=461 [M+H]+, RT=4.52 min.

Workup

  1. stirringThe reaction mixture was then stirred at room temperature overnight
  2. customThe mixture was purified

Sources & evidence

ORD record
ord-52847c2e11d04c0fa03f07a9df7d5bdd
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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