(E)-tert-Butyl 4-(5-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate → tert-Butyl 4-(5-(8-morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

HRID 1772631Notes

Reaction equation

HRID 1772631 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:32]=[C:33](/[CH:35]=[CH:36]/[C:37]4[CH:46]=[CH:45][C:44]5[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=5)[N:38]=4)[N:34]=3)[C:10]([C:13]3[CH:14]=[CH:15][C:16]([N:19]4[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]4)=[N:17][CH:18]=3)=[CH:11][N:12]=2)[CH2:3][CH2:2]1>CO>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:32]=[C:33]([CH2:35][CH2:36][C:37]4[CH:46]=[CH:45][C:44]5[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=5)[N:38]=4)[N:34]=3)[C:10]([C:13]3[CH:14]=[CH:15][C:16]([N:19]4[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH2:23][CH2:24]4)=[N:17][CH:18]=3)=[CH:11][N:12]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 86346129(E)-tert-Butyl 4-(5-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 86345487tert-Butyl 4-(5-(8-morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 19b (130 mg, 0.210 mmol) in MeOH (50 mL) was evacuated and back flushed with Argon gas three times before Pd/C (10%, 100 mg) was added. The mixture was evacuated and back flushed with H2, and was stirred at rt under H2 (in a balloon) for 3 h. The reaction mixture was filtered through a pad of diatomaceous earth, and the filtrate was concentrated under reduced pressure to leave a brown oil, which was purified by flash column chromatography on silica gel, eluting with EtOAc/heptane (0-100%). Compound 20a was obtained as an off-white solid (69.0 mg, 53% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C35H40N8O3: 621.3 (M+H). found: 621.4.

Workup

  1. customback flushed with Argon gas three times before Pd/C (10%, 100 mg)
  2. additionwas added
  3. customThe mixture was evacuated
  4. customback flushed with H2
  5. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customto leave a brown oil, which
  8. customwas purified by flash column chromatography on silica gel
  9. washeluting with EtOAc/heptane (0-100%)

Sources & evidence

ORD record
ord-97204919972c48f18b65e53535ae7640
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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