Hydrochloric Acid → HCID 178518664, compound

HRID 388139Notes

Reaction equation

HRID 388139 reaction equation
Cl.[N:2]1[N:3]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:18]=[C:17]4[N:19]([CH2:23][CH2:24][N:25]5[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]5)[C:20](=[O:22])[NH:21][C:16]4=[N:15][CH:14]=3)=[CH:9][CH:8]=2)[NH:5][CH:6]=1.Cl.O=C1NC2=NC=C(C3C=CC(C(=N)OCC)=CC=3)N=C2N1CCN1CCCCC1.C(NN)=O.C(N(CC)CC)C.Cl>CO.CCOCC>[N:2]1[N:3]=[C:4]([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[N:18]=[C:17]4[N:19]([CH2:23][CH2:24][N:25]5[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]5)[C:20](=[O:22])[NH:21][C:16]4=[N:15][CH:14]=3)=[CH:11][CH:12]=2)[NH:5][CH:6]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12229HydrazinecarboxaldehydeHCID 66699921HCID 66699921, compoundHCID 178479658HCID 178479658, compound

Product 1

HCID 178518664HCID 178518664, compoundYield 8.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

6-(4-(4H-1,2,4-triazol-3-yl)phenyl)-1-(2-(piperidin-1-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride. Ethyl 4-(2-oxo-3-(2-(piperidin-1-yl)ethyl)-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-5-yl)benzimidate hydrochloride (0.4 g., 1.01 mmol), formic hydrazide (0.183 g., 3.04 mmol) and triethylamine (0.42 mL, 3.04 mmol) were combined in methanol (4 mL) and heated in a sealed tube at 100° C. for 3 h. The reaction mixture was cooled to room temperature and purified by reverse-phase semi-preparatory HPLC (5-100% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min). The clean fractions were collected and concentrated and the solid obtained was treated with hydrochloric acid in ether, filtered and dried under high vacuum to yield the title compound (0.035 g., 8.1% yield). 1H NMR (400 MHz, DMSO-d6+D2O) δ 8.64 (s, 1H), 8.50(s, 1H), 8.20 (d, J=8.4, 2H), 8.15 (d, J=8.4, 2H), 4.34 (m, 2H), 3.76 (d, J=10.8, 2H), 3.53 (m, 2H), 2.98 (t, J=10.8, 2H), 1.86 (m, 2H),1.70 (m, 2H), 1.5 (m, 2H); MS (ESI) m/z 391.5[M+1]+; mp 194-197° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompurified by reverse-phase semi-preparatory HPLC (5-100% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min)
  3. customThe clean fractions were collected
  4. concentrationconcentrated
  5. customthe solid obtained
  6. filtrationfiltered
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-83de438d8720471bab05c14aca3c5429
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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