Acetic Acid → HCID 67028846, compound

HRID 455116Notes

Reaction equation

HRID 455116 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:18][NH:19][C:20]3[N:25]=[C:24]([CH:26]=O)[CH:23]=[CH:22][N:21]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[C:28](O)(=O)C.[CH2:32]([NH2:34])[CH3:33].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH2:32]([NH:34][CH2:26][C:24]1[CH:23]=[CH:22][N:21]=[C:20]([NH:19][CH2:18][C:8]2[N:6]3[CH:7]=[C:2]([CH3:28])[CH:3]=[CH:4][C:5]3=[N:10][C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:25]=1)[CH3:33]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86655126HCID 86655126, compound

Product 1

HCID 67028846HCID 67028846, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-((6-chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl)methylamino)pyrimidine-4-carbaldehyde (110 mg, 0.29 mmol) in CH2Cl2 (5 mL) was added acetic acid (0.5 mL) until the reaction became clear. Ethylamine (0.87 mmol, 3.0 eq) and Na(OAc)3BH (0.58 mmol, 2.0 eq) were added and the reaction mixture was stirred for 18 h at room temperature. After this time the reaction was diluted with CH2Cl2 (20 mL) and quenched by the addition of satd. aq. NaHCO3 (10 mL). After stirring for 10 min the layers were separated and the organic layer was dried over Na2SO4, filtered, concentrated and purified by reverse phase preparatory HPLC (silica gel, acetonitrile/water w/0.05% TFA) to afford the desired product. (0.060 g, 37% yield). M/e+ 411.1 for C21H20ClFN6 (M+H)+; 1H-NMR (500 MHz, CDCl3, δ) 8.48 (d, J=1.5 Hz, 1H), 8.29 (d, J=5.0 Hz, 1H), 7.78-7.75 (m, 2H), 7.58 (d, J=9.5 Hz, 1H), 7.21-7.15 (m, 3H), 6.70 (d, J=5.5 Hz, 1H), 5.24 (br s, 1H), 5.05 (d, J=5.5 Hz, 2H), 3.77 (s, 2H), 2.72 (q, J=7.5 Hz, 2H), 1.15 (t, J=7.5 Hz, 3H).

Workup

  1. customquenched by the addition of satd
  2. stirringAfter stirring for 10 min the layers
  3. customwere separated
  4. dry with materialthe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by reverse phase preparatory HPLC (silica gel, acetonitrile/water w/0.05% TFA)

Sources & evidence

ORD record
ord-f47d44d6f1e94ee283daa4d393524554
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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