HCID 86345607, compound → 4-(5-(6-(Piperazin-1-yl)pyridin-3-yl)-2-(1-(quinolin-2-yl)azetidin-3-yl)imidazo[1,2-a]pyrazin-8-yl)morpholine

HRID 1772655Notes

Reaction equation

HRID 1772655 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:35]=[C:36]([CH:38]4[CH2:41][N:40]([C:42]5[CH:51]=[CH:50][C:49]6[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=6)[N:43]=5)[CH2:39]4)[N:37]=3)[C:10]([C:13]3[CH:14]=[CH:15][C:16]([N:19]4[CH2:24][CH2:23][N:22](C(OCC5C=CC=CC=5)=O)[CH2:21][CH2:20]4)=[N:17][CH:18]=3)=[CH:11][N:12]=2)[CH2:3][CH2:2]1>CO.C(Cl)Cl.[Pd]>[N:19]1([C:16]2[N:17]=[CH:18][C:13]([C:10]3[N:9]4[CH:35]=[C:36]([CH:38]5[CH2:39][N:40]([C:42]6[CH:51]=[CH:50][C:49]7[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=7)[N:43]=6)[CH2:41]5)[N:37]=[C:8]4[C:7]([N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)=[N:12][CH:11]=3)=[CH:14][CH:15]=2)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1

Participants

5

Reactant 1

HCID 86345607HCID 86345607, compound

Product 1

HCID 863456064-(5-(6-(Piperazin-1-yl)pyridin-3-yl)-2-(1-(quinolin-2-yl)azetidin-3-yl)imidazo[1,2-a]pyrazin-8-yl)morpholine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 29d (100 mg, 0.147 mmol) in MeOH (15 mL) and DCM (5 mL) was hydrogenated over 10% Pd/C (20 mg) overnight under balloon pressure. The reaction mixture was filtered through a pad of diatomaceous earth and the filtrate was concentrated and dried under reduced pressure to obtain the title compound 99. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 8.36 (d, J=2.3 Hz, 1H), 8.04 (d, J=9.0 Hz, 1H), 7.84-7.92 (m, 2H), 7.71 (d, J=7.8 Hz, 1H), 7.49-7.60 (m, 2H), 7.33-7.37 (m, 1H), 7.19-7.25 (m, 1H), 7.03 (d, J=8.6 Hz, 1H), 6.77 (d, J=9.0 Hz, 1H), 5.77 (s, 1H), 4.44-4.52 (m, 2H), 4.24 (t, J=6.8 Hz, 2H), 4.10-4.20 (m, 4H), 3.68-3.78 (m, 8H), 3.36 (br. s., 2H), 2.97-3.10 (m, 2H), 2.56 (br. s., 1H). Mass Spectrum (LCMS, ESI pos.) Calcd. for C31H33N9O: 548.3 (M+H). Found 548.3.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. concentrationthe filtrate was concentrated
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-f0ec4d56d0f04ee8a37cd512b67f9349
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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