Ammonia → HCID 11212718, compound

HRID 2373892Notes

Reaction equation

HRID 2373892 reaction equation
[NH3:1].CO[C:4](=[O:35])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19](Cl)[C:14]3=[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:22]=3)[N:12]=2)[CH:6]=1.[NH3:36].CC(O)C>>[NH2:1][C:19]1[C:14]2[N:15]([C:11]([C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=3)[C:4]([NH2:36])=[O:35])=[N:12][C:13]=2[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:22]=2)[CH:16]=[CH:17][N:18]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 59852731HCID 59852731, compound

Product 1

HCID 11212718HCID 11212718, compound

Conditions

Temperature
110 °C

Procedure

Gaseous NH3 was condensed into a cooled (−78° C.) solution of 3-[1-(3-benzyloxyphenyl)-8-chloroimidazo[1,5-a]pyrazin-3-yl]-benzoic acid methyl ester (102 mg, 0.216 mmol) in NH3/i-PrOH (2M, 3 mL) in a pressure tube until the volume had doubled. The tube was sealed and heated to 110° C. for 2 d. After excess NH3/i-PrOH was removed in vacuo, the crude material was taken up in CH2Cl2, adsorbed onto Hydromatrix, and purified by chromatography on silica gel [Jones Flashmaster, 5 g/25 mL cartridge, eluting with MeOH:CH2Cl2 1%→5%], yielding the title compound, as an off-white solid; 1H NMR (d-DMSO, 400 MHz) δ 5.18 (s, 2H), 6.30 (s, br, —NH2), 7.10-7.18 (m, 2H), 7.25-7.58 (m, 9H), 7.67 (t, J=7.6 Hz, 1H), 7.81 (d, J=4.4 Hz, 1H), 8.00 (d, J=7.6 Hz, 2H), 8.16 (s, 1H), 8.31 (s, 1H); MS (ES+): m/z 436.0 (100) [MH+].

Workup

  1. customcondensed into
  2. customThe tube was sealed
  3. customAfter excess NH3/i-PrOH was removed in vacuo
  4. custompurified by chromatography on silica gel [Jones Flashmaster, 5 g/25 mL cartridge, eluting with MeOH:CH2Cl2 1%→5%]

Sources & evidence

ORD record
ord-151ea683d7ba417786b21d82e97c439b
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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