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Methanol → HCID 59410702, compound

HRID 912540
Notes
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Reaction equation

HRID 912540 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][N:7]1[C:15]2[CH:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[C:18]([C:31]([F:34])([F:33])[F:32])[CH:17]=3)[N:12]=[C:11]([C:35]#[N:36])[C:10]=2[N:9]=[CH:8]1.CCN(C(C)C)C(C)C.CO>C(Cl)Cl.C1COCC1.C(Cl)Cl.C(OCC)(=O)C>[Cl:1][CH2:2][C:3]([N:28]1[CH2:29][CH2:30][CH:25]([CH2:24][CH2:23][O:22][C:19]2[CH:20]=[CH:21][C:16]([C:13]3[N:12]=[C:11]([C:35]#[N:36])[C:10]4[N:9]=[CH:8][N:7]([CH3:6])[C:15]=4[CH:14]=3)=[CH:17][C:18]=2[C:31]([F:33])([F:32])[F:34])[CH2:26][CH2:27]1)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 887MethanolHCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 498621461-methyl-6-(4-(2-(piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Product 1

HCID 59410702HCID 59410702, compound

Reagents, catalysts & solvents 3

HCID 6344
Dichloromethane
Solvent
HCID 8857Ethyl AcetateSolvent
HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

Chloroacetylchloride (0.323 ml) in 1 ml DCM was added at 0° C. to the suspension of 1-methyl-6-(4-(2-(piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (free base) in THF/DCM (1:1, 40 ml) with DIPEA (1.7 ml). The mixture was stirred at rt for 2 hours, then 10 ml methanol added, followed by 200 ml ethyl acetate. The mixture was washed with water (100 ml), sodium bicarbonate (100 ml), dried, filtered, solvent removed, residue was columned on silica gel using 100:5 DCM/MeOH as eluant to give 0.7 g product as off white solid. 1H NMR (CD3OD) δ: 8.25 (d, 1H), 8.22 (s, 1H), 8.10 (s, 1H), 7.87 (s, 1H), 7.10 (d, 1H), 4.58 (m, 1H), 4.21 (t, 2H), 4.09 (d, 1H), 4.08 (d, 1H), 3.99 (s, 3H), 3.90 (m, 1H), 3.12 (t, 1H), 2.65 (t, 1H), 2.2 (m, 1H), 1.8-2.0 (m, 4H), 1.1-1.4 (m, 2H).

Workup

  1. washThe mixture was washed with water (100 ml), sodium bicarbonate (100 ml)
  2. customdried
  3. filtrationfiltered
  4. customsolvent removed

Sources & evidence

ORD record
ord-11326172a5d542a7a9e9ef31d053a282
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08026236B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes