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2-Chloroaniline → HCID 89783333, compound

HRID 1055932
Notes
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Reaction equation

HRID 1055932 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]3[NH:20][C:19]4[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=4[CH:13]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Cl:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C(=O)=O.CO.CCO.CC(O)C.[NH4+].[OH-]>[Cl:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH:25][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]3[NH:20][C:19]4[CH:18]=[CH:17][NH:16][C:15](=[O:21])[C:14]=4[CH:13]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 3

HCID 72402-ChloroanilineHCID 2733832Lithium hexamethyldisilazaneHCID 897835482-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 89783333HCID 89783333, compoundYield 14%

Reagents, catalysts & solvents 5

HCID 280Carbon DioxideSolvent
HCID 702
Ethanol
Solvent
HCID 887MethanolSolvent
HCID 3776IsopropanolSolvent
HCID 14923Ammonium HydroxideSolvent

Procedure

A solution of 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 53.5 mg, 0.180 mmol), 2-chloroaniline (94 μl, 0.898 mmol), and LHMDS (1.0 M in THF; 898 μl, 0.898 mmol) was stirred in a sealed flask at 65° C. for 4 h. The mixture was then partitioned between DCM (50 mL) and saturated aq. NH4Cl (30 mL). The organic layer was separated, and the aq. layer was extracted with DCM (2×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by supercritical-fluid chromatography (Chiralcel OJ-H (250×21 mm, 5 μm), 55% liquid CO2/45% 1:1:1 MeOH:EtOH:IPA (+20 mM aq. NH4OH), 75 mL/min) separately provided 2-(2-((2-chlorophenyl)amino)-quinolin-8-yl)-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (107; 9.7 mg, 0.025 mmol, 14% yield; first-eluting compound) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 12.47 (1H, br. s.), 9.73 (1H, br. s.), 8.17 (2H, t, J=8.9 Hz), 8.06 (1H, d, J=9.0 Hz), 7.59 (2H, t, J=7.6 Hz), 7.39 (3H, quin, J=7.8 Hz), 7.22 (1H, t, J=7.6 Hz), 6.99 (2H, d, J=8.6 Hz), 6.94 (1H, s), 6.08 (1H, d, J=7.0 Hz). m/z (ESI, +ve) 387.0 (M+H)+: and 2-(2-((2-chlorophenyl)amino)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (108; 14.0 mg, 0.036 mmol, 20% yield; second-eluting compound) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 12.16 (1H, s), 8.04 (3H, t, J=8.7 Hz), 7.53 (2H, d, J=8.0 Hz), 7.35-7.41 (1H, m), 7.31 (2H, t, J=7.8 Hz), 7.09-7.18 (2H, m), 6.95 (1H, d, J=8.8 Hz), 5.32 (1H, br. s.), 3.53-3.60 (2H, m), 2.68 (2H, br. s.). m/z (ESI, +ve) 389.1 (M+H)+.

Workup

  1. customThe mixture was then partitioned between DCM (50 mL) and saturated aq. NH4Cl (30 mL)
  2. customThe organic layer was separated
  3. extractionthe aq. layer was extracted with DCM (2×20 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa8839ca87b64a4684d9e915f437d28b
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394297B2

Reaction notes

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