Acetic Acid → HCID 72706323, compound

HRID 926123Notes

Reaction equation

HRID 926123 reaction equation
[C:1]([C:4]1[CH:13]=[N:12][C:11]2[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:9](=[O:23])[N:8]3[N:24]=[CH:25][N:26]=[C:7]3[C:6]=2[CH:5]=1)(=O)[CH3:2].[CH3:27][C@@H:28]1[O:33][C@H:32]([CH3:34])[CH2:31][NH:30][CH2:29]1.C(O)(=O)C.C([BH3-])#N.[Na+]>C(#N)C>[CH3:27][C@H:28]1[CH2:29][N:30]([CH:1]([C:4]2[CH:13]=[N:12][C:11]3[N:10]([CH2:14][C:15]4[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=4)[C:9](=[O:23])[N:8]4[N:24]=[CH:25][N:26]=[C:7]4[C:6]=3[CH:5]=2)[CH3:2])[CH2:31][C@@H:32]([CH3:34])[O:33]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6415002,6-Dimethylmorpholine, cis-HCID 5003444Sodium cyanoborohydrideHCID 86705394HCID 86705394, compound

Product 1

HCID 72706323HCID 72706323, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

9-Acetyl-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 81, 67 mg, 0.19 mmol), (2S,6R)-2,6-dimethylmorpholine (0.060 mL, 0.49 mmol), ACN (1 mL) and acetic acid (0.020 mL, 0.35 mmol) were combined and stirred for 10 minutes. Sodium cyanoborohydride (18 mg, 0.29 mmol) was added and the mixture was stirred for 3 days at 50° C. The mixture was filtered. Purification (HPLC, 10-65% ACN in water) afforded the title compound (26 mg, 23%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.19 (d, J=6.27 Hz, 3H), 1.23 (d, J=6.27 Hz, 3H), 1.92 (d, J=7.03 Hz, 3H), 2.34 (td, J=11.01, 2.32 Hz, 2H), 3.32 (d, J=11.42 Hz, 1H), 3.57 (d, J=11.42 Hz, 1H), 3.77 (s, 3H), 4.12 (d, J=7.03 Hz, 2H), 4.54 (q, J=6.86 Hz, 1H), 5.75 (s, 2H), 6.85 (d, J=8.66 Hz, 2H), 7.62 (d, J=8.66 Hz, 2H), 8.40 (s, 1H), 8.74 (s, 1H), 8.95 (s, 1H). [M+H]=449.3.

Workup

  1. stirringthe mixture was stirred for 3 days at 50° C
  2. filtrationThe mixture was filtered
  3. customPurification (HPLC, 10-65% ACN in water)

Sources & evidence

ORD record
ord-365350ec378947709b918c62cf386b42
Source dataset
uspto-grants-2016_03
Patent number
US09284335B2

Reaction notes

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