Diisopropylethylamine → HCID 58369003, compound

HRID 2061175Notes

Reaction equation

HRID 2061175 reaction equation
[CH3:1][CH:2]([CH2:6][O:7][Si](C(C)C)(C(C)C)C(C)C)[C:3]([OH:5])=O.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.[CH3:51][N:52]1[C:61]2[C:56](=[CH:57][N:58]=[C:59]([CH3:62])[CH:60]=2)[CH:55]=[C:54]([C:63]2[CH:64]=[C:65]([NH:70]/[C:71](/[NH2:74])=[N:72]/O)[CH:66]=[CH:67][C:68]=2[CH3:69])[C:53]1=[O:75].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CN(C=O)C>[OH:7][CH2:6][CH:2]([C:3]1[O:5][N:72]=[C:71]([NH:70][C:65]2[CH:66]=[CH:67][C:68]([CH3:69])=[C:63]([C:54]3[C:53](=[O:75])[N:52]([CH3:51])[C:61]4[C:56]([CH:55]=3)=[CH:57][N:58]=[C:59]([CH3:62])[CH:60]=4)[CH:64]=2)[N:74]=1)[CH3:1]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 2724141Tetrabutylammonium FluorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58369044HCID 58369044, compoundHCID 178422078HCID 178422078, compound

Product 1

HCID 58369003HCID 58369003, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-Methyl-3-(triisopropylsilyloxy)propanoic acid (34 mg, 0.12 mmol), HATU (50 mg, 0.12 mmol), and DIPEA (0.023 mL, 0.12 mmol) were stirred in dry DMF (3 mL) for 1 h before 17 (40 mg, 0.118 mmol) was added at rt. The stirring was continued for 1 h before it was heated at 100° C. for 5 h. After cooling, TBAF (1 ml, 1 M in THF) was added and stirred for 5 h at rt. After filtration, the mixture was purified by preparative LC/MS to give 3-(5-(5-(1-hydroxypropan-2-yl)-1,2,4-oxadiazol-3-ylamino)-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one (A67) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 9.06 (s, 1H), 8.03 (s, 1H), 7.91 (s, 1H), 7.42 (d, J=2.4 Hz, 1H), 7.35 (dd, J=2.4, 8.0 Hz, 1H), 7.23 (d, J=8.4 Hz, 1H), 3.82 (m, 2H), 3.35 (s, 3H), 3.18 (m, 1H), 2.86 (s, 3H), 2.16 (s, 3H), 1.35 (d, J=7.2 Hz, 3H). MS m/z 406.2 (M+1).

Workup

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

Sources & evidence

ORD record
ord-a6f48132a6934408a85cdb36b3a2857e
Source dataset
uspto-grants-2012_10
Patent number
US08278452B2

Reaction notes

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