Hydrochloric Acid → HCID 16753773, compound

HRID 1992443Notes

Reaction equation

HRID 1992443 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][S:6][C:7]1[N:11]2[CH:12]=[CH:13][N:14]=[C:15]([NH2:16])[C:10]2=[C:9]([C:17]2[NH:18][C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:8]=1)C.Cl>>[NH2:16][C:15]1[C:10]2[N:11]([C:7]([S:6][CH2:5][C:4]([OH:26])=[O:3])=[N:8][C:9]=2[C:17]2[NH:18][C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:12]=[CH:13][N:14]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 16753774HCID 16753774, compound

Product 1

HCID 16753773HCID 16753773, compoundYield 90%

Procedure

A solution of [8-amino-1-(1H-indol-2-yl)-imidazo[1,5-a]pyrazin-3-ylsulfanyl]-acetic acid ethyl ester (6.7 mg, 0.000018 mol) and conc. HCl (3.0 mL) was stirred at rt for 5 h. The conc. HCl was removed in vacuo to afford 6 mg, 90% yield, of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm =4.12 (s, 2H), 6.82 (s, 1H), 7.07 (t, J=7.83, 7.07 Hz, 11H), 7.14-7.22 (m, 2H), 7.48 (d, J=8.08 Hz, 11H), 7.63 (d, J=7.83 Hz, 11H), 7.71 (d, J=5.56 Hz, 1H) and 11.75 (s, 1H); MS (ES+): m/z 339.92 [M+]. HPLC: tR=1.94 min (OpenLynx: polar—5 min).

Workup

  1. customThe conc. HCl was removed in vacuo
  2. customto afford 6 mg, 90% yield

Sources & evidence

ORD record
ord-87773d694fdd4385b0873fbaf6a81846
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

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