Acetic Anhydride → HCID 11677004, compound

HRID 244109Notes

Reaction equation

HRID 244109 reaction equation
Cl.Cl.Cl.[C:4]1([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][C:14]([C:20]4[N:21]=[C:22]([CH:30]5[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]5)[N:23]5[CH:28]=[CH:27][N:26]=[C:25]([NH2:29])[C:24]=45)=[CH:15][CH:16]=3)[N:11]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:36](OC(=O)C)(=[O:38])[CH3:37]>C(N(CC)CC)C.CN(C=O)C>[NH2:29][C:25]1[C:24]2[N:23]([C:22]([CH:30]3[CH2:35][CH2:34][N:33]([C:36](=[O:38])[CH3:37])[CH2:32][CH2:31]3)=[N:21][C:20]=2[C:14]2[CH:13]=[C:12]3[C:17]([CH:18]=[CH:19][C:10]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=4)=[N:11]3)=[CH:16][CH:15]=2)[CH:28]=[CH:27][N:26]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 66676486HCID 66676486, compound

Product 1

HCID 11677004HCID 11677004, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

1-(2-Phenyl-quinolin-7-yl)-3-piperidin-4-yl-imidazo[1,5-a]pyrazin-8-ylamine-tris HCl salt (59.0 mg, 0.1 mmol) was dissolved in triethylamine (1.0 mL) and DMF (0.5 mL). Acetic anhydride (12.0 μL, 0.1 mmol) was added and the reaction was stirred for 1 h. The reaction was concentrated in vacuo and purified by silica gel chromatography (Jones Flashmaster, 2 g/12 mL cartridge, eluting with 2% 7N NH3 in methanol/CH2Cl2). The sample was further purified using MDPS to yield 1-{4-[8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl}ethanone as a pale yellow solid; 1H NMR (CDCl3, 400 MHz) δ 1.95 (ddd, 1H, J=22.4, 11.2, 4.0 Hz), 2.03-2.23 (m, 6H), 2.90 (ddd, 1H, J=13.6, 13.6, 2.8 Hz), 3.19-3.32 (m, 2H), 4.01 (bd, 1H, J=13.6 Hz), 4.64 (bd, 1H, J=13.2 Hz), 5.44 (bs, 2H), 7.11 (d, 1H, J=4.8 Hz), 7.24 (d, 1H, J=5.6 Hz), 7.46 (ddd, 1H, J=6.0, 2.4, 0.8 Hz), 7.50-7.54 (m, 2H), 7.86-7.94 (m, 3H), 8.16 (ddd, 2H, J=7.2, 3.6, 1.6 Hz), 8.24 (d, 1H, J=8.4 Hz), 8.38 (s, 1H); MS (ES+): m/z 463 (10) [MH+]; HPLC: tR=2.1 min (OpenLynx, polar—5 min).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by silica gel chromatography (Jones Flashmaster, 2 g/12 mL cartridge, eluting with 2% 7N NH3 in methanol/CH2Cl2)
  3. customThe sample was further purified

Sources & evidence

ORD record
ord-5b19bd2c6930439896ff062505fc1fa2
Source dataset
uspto-grants-2014_02
Patent number
US08653268B2

Reaction notes

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