Ethyl isocyanate → HCID 11699062, compound

HRID 386196Notes

Reaction equation

HRID 386196 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][C:11]([C:17]4[N:18]=[C:19]([CH2:27][CH:28]5[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]5)[N:20]5[CH:25]=[CH:24][N:23]=[C:22]([NH2:26])[C:21]=45)=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:34]([N:36]=[C:37]=[O:38])[CH3:35]>C(Cl)Cl>[CH2:34]([NH:36][C:37]([N:31]1[CH2:32][CH2:33][CH:28]([CH2:27][C:19]2[N:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH2:26])[C:21]3=[C:17]([C:11]3[CH:10]=[C:9]4[C:14]([CH:15]=[CH:16][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[N:8]4)=[CH:13][CH:12]=3)[N:18]=2)[CH2:29][CH2:30]1)=[O:38])[CH3:35]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 11517695HCID 11517695, compound

Product 1

HCID 11699062HCID 11699062, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-Phenylquinolin-7-yl)-3-(piperidin-4-ylmethyl)-imidazo-[1,5-a]-pyrazin-8-amine (110.00 mg, 0.25 mmol) in a dried 15 mL round-bottom flask was dissolved in 2.00 mL of CH2Cl2. At four 15 min. increments, 10 μL (0.47 equiv), 5 μL (0.24 equiv), 2.1 μL (0.1 equiv) and 2.1 μL (0.1 equiv) of ethylisocyanate were added dropwise, respectfully. The crude product was purified by 5 g Jones silica gel (wetted with 100% CH2Cl2; dry loaded with silica gel, eluted with 2% (7N NH3) in MeOH/CH2Cl2→5% (7N NH3) in MeOH/CH2Cl2) and afforded the desired product; 1H NMR (400 MHz, CHLOROFORM-d) δ 8.41 (1 H, d, J=1.64), 8.29 (1 H, d, J=8.38), 8.20 (2 H, dd, J=1.52, J=1.10), 7.97 (2 H, m), 7.87 (1 H, dd, J=1.71, J=1.71), 7.53 (4 H, m), 7.24 (1 H, d, J=5.26), 7.08 (1 H, d, J=5.23), 4.38 (1 H, t), 3.97 (2 H, d, J=13.44), 3.28 (2 H, m), 2.96 (2 H, d, J=7.12), 2.79 (2 H, t), 2.20 (1 H, m), 1.80 (2 H, d, J=10.60), 1.36 (2 H, m); MS (ES+): m/z 506.07/507.08 (50/25) [MH+]; HPLC: tR=2.17 min (OpenLynx, polar—5 min).

Workup

  1. customThe crude product was purified by 5 g Jones silica gel (wetted with 100% CH2Cl2; dry loaded with silica gel, eluted with 2% (7N NH3) in MeOH/CH2Cl2→5% (7N NH3) in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-573685ecd9c1408ca70fae06a09603b9
Source dataset
uspto-grants-2013_02
Patent number
US08367826B2

Reaction notes

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