Diisopropylethylamine → HCID 44200989, compound

HRID 2061168Notes

Reaction equation

HRID 2061168 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:44][N:45]1[C:54]2[C:49](=[CH:50][N:51]=[C:52]([CH3:55])[CH:53]=2)[CH:48]=[C:47]([C:56]2[CH:57]=[C:58]([NH:63]/[C:64](/[NH2:67])=[N:65]/O)[CH:59]=[CH:60][C:61]=2[CH3:62])[C:46]1=[O:68]>CN(C=O)C>[CH3:44][N:45]1[C:54]2[C:49](=[CH:50][N:51]=[C:52]([CH3:55])[CH:53]=2)[CH:48]=[C:47]([C:56]2[CH:57]=[C:58]([NH:63][C:64]3[N:65]=[C:6]([C:5]4[CH:4]=[N:3][C:2]([CH3:1])=[CH:10][CH:9]=4)[O:8][N:67]=3)[CH:59]=[CH:60][C:61]=2[CH3:62])[C:46]1=[O:68]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1378606-Methylnicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178422078HCID 178422078, compound

Product 1

HCID 44200989HCID 44200989, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6-Methylnicotinic acid (0.67 g, 4.89 mmol), HATU (1.86 g, 4.89 mmol), and DIPEA (0.85 mL, 4.89 mmol) were stirred in dry DMF (20 mL) for 1 h before 17 (1.5 g, 4.44 mmol) was added at rt. The stirring was continued for 1 h before it was heated at 100° C. for 5 h. After cooling and filtration, the mixture was purified by preparative LC/MS to give 1,7-dimethyl-3-(2-methyl-5-(5-(6-methylpyridin-3-yl)-1,2,4-oxadiazol-3-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one (A51) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 9.27 (d, J=2.0 Hz, 1H), 9.10 (s, 1H), 8.73 (dd, J=2.0, 8.4 Hz, 1H), 8.07 (s, 1H), 7.94 (s, 1H), 7.85 (d, J=8.4 Hz, 1H), 7.50 (d, J=2.4 Hz, 1H), 7.46 (dd, J=2.4, 8.4 Hz, 1H), 7.29 (d, J=8.4 Hz, 1H), 3.85 (s, 3H), 2.87 (s, 3H), 2.79 (s, 3H), 2.19 (s, 3H). MS m/z 439.2 (M+1).

Workup

  1. additionwas added at rt
  2. temperatureAfter cooling
  3. filtrationfiltration
  4. customthe mixture was purified by preparative LC/MS

Sources & evidence

ORD record
ord-70d9d823a22c4cb9b3af455fe5cf916d
Source dataset
uspto-grants-2012_10
Patent number
US08278452B2

Reaction notes

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