Diisopropylethylamine → HCID 44199701, compound

HRID 2061181Notes

Reaction equation

HRID 2061181 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([OH:8])=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.[CH3:42][N:43]1[C:52]2[C:47](=[CH:48][N:49]=[C:50]([CH3:53])[CH:51]=2)[CH:46]=[C:45]([C:54]2[CH:55]=[C:56]([NH:61]/[C:62](/[NH2:65])=[N:63]/O)[CH:57]=[CH:58][C:59]=2[CH3:60])[C:44]1=[O:66]>CN(C=O)C>[CH3:42][N:43]1[C:52]2[C:47](=[CH:48][N:49]=[C:50]([CH3:53])[CH:51]=2)[CH:46]=[C:45]([C:54]2[CH:55]=[C:56]([NH:61][C:62]3[N:63]=[C:6]([C@@H:2]4[CH2:3][CH2:4][CH2:5][O:1]4)[O:8][N:65]=3)[CH:57]=[CH:58][C:59]=2[CH3:60])[C:44]1=[O:66]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 446666Tetrahydro-2-furoic acid, (-)-HCID 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 44199701HCID 44199701, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

(S)-Tetrahydrofuran-2-carboxylic acid (75.7 mg, 0.65 mmol), HATU (247 mg, 0.65 mmol), and DIPEA (0.11 mL, 0.65 mmol) were stirred in dry DMF (6 mL) for 1 h before 17 (200 mg, 0.59 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 (S)-1,7-dimethyl-3-(2-methyl-5-(5-(tetrahydrofuran-2-yl)-1,2,4-oxadiazol-3-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one (A77) as a solid. 1H NMR (400 MHz, d4-MeOH) δ 9.07 (s, 1H), 8.04 (s, 1H), 7.91 (s, 1H), 7.45 (d, J=4 Hz, 1H), 7.36 (dd, J=8, 4 Hz, 1H), 7.25 (d, J=4 Hz, 1H), 5.10 (dd, J=8, 4 Hz, 1H), 4.03 (dd, J=12, 8 Hz, 1H), 3.96 (dd, J=12, 8 Hz, 1H), 3.83 (s, 3H), 2.85 (s, 3H), 2.41-2.34 (m, 1H), 2.28-2.20 (m, 1H), 2.16 (s, 3H), 2.12-2.03 (m, 2H). MS m/z 417.5, 418.5 (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-46d5670ffb0a42329c082a44de808548
Source dataset
uspto-grants-2012_10
Patent number
US08278452B2

Reaction notes

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