2-Aminopyridine → HCID 44199050, compound

HRID 1971323Notes

Reaction equation

HRID 1971323 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1[CH:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:12][C:13](O)=[O:14].[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>C(Cl)(Cl)Cl>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1[CH:11]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:12][C:13]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)=[O:14]

Participants

6

Reactant 4

HCID 104392-AminopyridineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 188709533-(1-Oxo-1,3-dihydro-isoindole-2-yl)-3-phenyl-propionic acid

Product 1

HCID 44199050HCID 44199050, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-(1-Oxo-1,3-dihydro-isoindole-2-yl)-3-phenyl-propionic acid (0.42 mmol, 1 eq), 2-amino pyridine (1.5 eq), HBTU [2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphat], (1.5 eq) and N-ethyl diisopropylamine (1.5 eq) are suspended in chloroform and reacted in the microwave (90 min, 120° C., Emrys Optimizer). The resulting mixture is partitioned between chloroform and water. The organic phase is dried over Na2SO4, filtered and concentrated in vacuo. The crude product is dissolved in DMSO and purified by prep. LC/MS (reversed phase). 3-(1-Oxo-1,3-dihydro-isoindole-2-yl)-3-phenyl-N-pyridine-2-yl-propionamide (“A1”) is obtained as brown solid (36% yield); ES-MS (MH+)=358.2; 1H-NMR (DMSO-d6, 400 MHz): δ [ppm] 10.72 (s, 1H), 8.29 (d, 1H, 4.8 Hz), 7.97 (d, 1H, 8.3 Hz), 7.73-7.27 (m, 10H), 7.08-7.05 (m, 1H), 5.95-5.92 (m, 1H), 4.62 (d, 1H, 17.5 Hz), 4.18 (d, 1H, 17.5 Hz), 3.39-3.32 (m, 2H).

Workup

  1. customreacted in the microwave (90 min, 120° C., Emrys Optimizer)
  2. customThe resulting mixture is partitioned between chloroform and water
  3. dry with materialThe organic phase is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude product is dissolved in DMSO
  7. custompurified by prep

Sources & evidence

ORD record
ord-65e1ff92649b4334aa48da4ee0a4c627
Source dataset
uspto-grants-2013_04
Patent number
US08431602B2

Reaction notes

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