Acetic Acid → HCID 118135076, compound

HRID 926118Notes

Reaction equation

HRID 926118 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[C:13]3[N:14]=[CH:15][C:16]([CH:18]=O)=[CH:17][C:12]=3[C:11]3=[N:20][CH:21]=[N:22][N:10]3[C:9]2=[O:23])=[CH:5][CH:4]=1.[CH:26]12[CH2:32][CH:29]([NH:30][CH2:31]1)[CH2:28][O:27]2.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C(#N)C>[CH:26]12[CH2:32][CH:29]([N:30]([CH2:18][C:16]3[CH:15]=[N:14][C:13]4[N:8]([CH2:7][C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:25][CH:24]=5)[C:9](=[O:23])[N:10]5[N:22]=[CH:21][N:20]=[C:11]5[C:12]=4[CH:17]=3)[CH2:31]1)[CH2:28][O:27]2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 36145512-Oxa-5-azabicyclo(2.2.1)heptaneHCID 5003444Sodium cyanoborohydrideHCID 867053916-(4-Methoxybenzyl)-5-oxo-5,6-dihydropyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-9-carbaldehyde

Product 1

HCID 118135076HCID 118135076, compoundYield 55.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

6-(4-Methoxybenzyl)-5-oxo-5,6-dihydropyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-9-carbaldehyde (49 mg, 0.15 mmol), 2-oxa-5-azabicyclo[2.2.1]heptane (49 mg, 0.36 mmol), ACN (1 mL), TEA (0.051 mL, 0.37 mmol) and acetic acid (0.040 mL, 0.69 mmol) were combined and stirred for 10 minutes. Sodium cyanoborohydride (18 mg, 0.29 mmol) was added and the mixture was stirred for 18 h at room temperature. The mixture was diluted with methanol, filtered, and purified by preparative HPLC to afford the title compound (35 mg, 45%) as the trifluoroacetic acid salt as a white solid. 1H NMR (400 MHz, CDCl3) δ 2.25 (d, J=11.42 Hz, 1H), 2.43 (br s, 1H), 3.44-3.63 (m, 2H), 3.76 (s, 3H), 3.91 (d, J=10.42 Hz, 1H), 4.37-4.53 (m, 3H), 4.56-4.65 (m, 1H), 4.73 (s, 1H), 5.74 (s, 2H), 6.76-6.91 (m, 2H), 7.60 (d, J=8.78 Hz, 2H), 8.38 (s, 1H), 8.83 (s, 1H), 9.08 (s, 1H). [M+H]=419.2.

Workup

  1. stirringthe mixture was stirred for 18 h at room temperature
  2. filtrationfiltered
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-92a09c8abf2a4824b98483fc8db161ab
Source dataset
uspto-grants-2016_03
Patent number
US09284335B2

Reaction notes

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