Triethylamine → HCID 58869944, compound

HRID 1191699Notes

Reaction equation

HRID 1191699 reaction equation
COC(=O)[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:31])[CH2:12][S:13][CH:14]2[C:18]([CH3:19])=[C:17]([CH3:20])[C:16](=[O:21])[N:15]2[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[N:6][CH:5]=1.C1C=CC2N(O)N=NC=2C=1.NC1C=CC=CN=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CC#N>[CH3:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:15]2[C:16](=[O:21])[C:17]([CH3:20])=[C:18]([CH3:19])[CH:14]2[S:13][CH2:12][C:11]([NH:10][C:7]2[CH:8]=[CH:9][CH:4]=[CH:5][N:6]=2)=[O:31])=[CH:28][CH:27]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 104392-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16058694HCID 16058694, compound

Product 1

HCID 58869944HCID 58869944, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product from Example 1, Part C (200 mg, 0.6 mmol) was dissolved in 25 mL CH3CN, HOBt (48 mg, 0.3 mmol) was added, and stirring continued for 1 h. 2-Aminopyridine (88 mg, 0.9 mmol), triethylamine (0.18 mL, 1.26 mmol), and HATU (250 mg, 0.66 mmol) were added and the mixture was stirred at room temperature for 2 h. Solvent was evaporated and the title compound was isolated as a white solid by silica gel chromatography (140 mg, 56%). 1H NMR (400 MHz, CDCl3) δ 8.41 (br s, 1H), 8.29 (m, 1H), 8.13 (d, J=8 Hz, 1H), 7.70 (m, 1H), 7.22 (d, J=9 Hz, 2H), 7.06 (m, 1H), 6.83 (d, J=9 Hz, 2H), 5.07 (d, J=15 Hz, 1H), 4.62 (s, 1H), 4.15 (d, J=15 Hz, 1H), 3.77 (s, 3H), 2.90 (m, 2H), 1.95 (s, 3H), 1.84 (s, 3H). MS: m/z (MH+) 398.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 h
  2. customSolvent was evaporated

Sources & evidence

ORD record
ord-695caef5766b400cbbc7d16d68ff626e
Source dataset
uspto-grants-2014_03
Patent number
US08680122B2

Reaction notes

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