Propylamine → HCID 22612364, compound

HRID 844050Notes

Reaction equation

HRID 844050 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)[CH:2]=1.F[P-](F)(F)(F)(F)F.[N:24]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:28]2C=CC=[CH:32][C:27]=2N=N1.CCN(C(C)C)C(C)C.C(N)CC>CN(C)C=O>[CH2:28]([NH:24][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][CH:15]=[N:16][C:8]=1[O:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:27][CH3:32]

Participants

6

Reactant 4

HCID 7852PropylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22032862HCID 22032862, compound

Product 1

HCID 22612364HCID 22612364, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(pyridin-3-yloxy)-nicotinic acid (0.100 g 0.462 mmole), BOP (0.205 grams, 0.463 mmole) and DIEA (0.242 μl) in dimethylformamide (5 ml) was added n-propyl amine (40 μl, 0.486 mmole) and stirred for 4 hours at room temperature. The reaction was quenched with 10 μl water and extracted with ethyl acetate. The combined organics were washed with alternating portions of 5% citric acid and sat'd bicarb, dried over Na2SO4, filtered and concentrated to a product which was purified by chromatography on silica gel eluting with diethyl ether to give a white crystalline solid (0.068 g). M.P. 55-56° C.; 1H H NMR (400 mhz, CDCl3) d 0.98 (t, J=7.3 Hz, 3H), 1.61-1.70 (m, 2H), 3.45-3.50 (m, 2H), 7.19 (dd, J=7.5 Hz, 4.8 Hz, 1H), 7.38-7.41 (m, 1H), 7.52-7.55 (m, 1H), 7.72 (bs, 1H), 8.16 (dd, J=4.8 hz, 2.1 Hz, 1H), 8.52-8.63 (m, 3H).

Workup

  1. customThe reaction was quenched with 10 μl water
  2. extractionextracted with ethyl acetate
  3. washThe combined organics were washed with alternating portions of 5% citric acid
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to a product which
  7. customwas purified by chromatography on silica gel eluting with diethyl ether

Sources & evidence

ORD record
ord-5da841cb1f084f178f6f18fdffa1acfe
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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