Morpholine → HCID 178509938, compound

HRID 1875216Notes

Reaction equation

HRID 1875216 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[NH:13][CH:14]=[C:15]([CH:17]=O)[N:16]=2)=[O:11])=[C:4]([F:19])[C:3]=1[O:20][C:21]1[CH:26]=[C:25]([C:27]#[N:28])[CH:24]=[C:23]([Cl:29])[CH:22]=1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[NH:13][CH:14]=[C:15]([CH2:17][N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[N:16]=2)=[O:11])=[C:4]([F:19])[C:3]=1[O:20][C:21]1[CH:26]=[C:25]([C:27]#[N:28])[CH:24]=[C:23]([Cl:29])[CH:22]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 178509939HCID 178509939, compound

Product 1

HCID 178509938HCID 178509938, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-4-formyl-1H-imidazole-2-carboxamide (0.11 mmol), morpholine (0.020 mL, 0.22 mmol), NaBH(OAc)3 (0.047 g, 0.22 mmol) in CH2Cl2 (1.5 mL) was stirred at RT overnight. Sat'd NaHCO3 was added and the solution was extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered, and purified by Reverse-Phase HPLC (water:acetonitrile with 0.1% TFA) and silica gel chromatography to afford the title compound (0.006 g, 11%) as a white solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.55 (t, J=1.47 Hz, 1H), 7.36-7.42 (m, 2H), 7.28 (t, J=2.06 Hz, 1H), 7.22-7.25 (m, 1H), 7.20 (br. s., 1H), 4.63 (s, 2H), 3.65-3.75 (m, 4H), 3.54 (br. s., 2H), 2.44-2.60 (m, 4H). ES-LCMS: m/z 504.1, 506.0 (M+1).

Workup

  1. extractionthe solution was extracted with CH2Cl2
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. custompurified by Reverse-Phase HPLC (water:acetonitrile with 0.1% TFA) and silica gel chromatography

Sources & evidence

ORD record
ord-44ab454c41ba46e3a605147be987fc3d
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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