2-Morpholinoethylamine → HCID 118093785, compound

HRID 1056993Notes

Reaction equation

HRID 1056993 reaction equation
[F:1][C:2]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:3]=1[O:4][C:5]1[C:10]2[NH:11][C:12](=[O:14])[NH:13][C:9]=2[C:8]([CH:15]=O)=[CH:7][C:6]=1[C:17]1[C:18]2[CH:27]=[CH:26][N:25]([S:28]([C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)(=[O:30])=[O:29])[C:19]=2[C:20](=[O:24])[N:21]([CH3:23])[CH:22]=1.[NH2:43][CH2:44][CH2:45][N:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1.C([BH3-])#N.[Na+]>CO.C(Cl)Cl.C(#N)C.O>[F:1][C:2]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:3]=1[O:4][C:5]1[C:10]2[NH:11][C:12](=[O:14])[NH:13][C:9]=2[C:8]([CH2:15][NH:43][CH2:44][CH2:45][N:46]2[CH2:51][CH2:50][O:49][CH2:48][CH2:47]2)=[CH:7][C:6]=1[C:17]1[C:18]2[CH:27]=[CH:26][N:25]([S:28]([C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)(=[O:30])=[O:29])[C:19]=2[C:20](=[O:24])[N:21]([CH3:23])[CH:22]=1

Participants

8

Reactant 3

HCID 4082852-MorpholinoethylamineHCID 5003444Sodium cyanoborohydride2×HCID 118093939HCID 118093939, compound

Product 1

HCID 118093785HCID 118093785, compoundYield 40%

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 887MethanolSolvent2×HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 7-(2,4-difluorophenoxy)-6-{6-methyl-1-[(4-methylphenyl)sulfonyl]-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl}-2-oxo-2,3-dihydro-1H-benzimidazole-4-carbaldehyde (25.0 mg, 0.0423 mmol) and N-(2-aminoethyl)morpholine (0.0111 mL, 0.0847 mmol) in methanol (0.40 mL) and methylene chloride (0.40 mL) was heated to 60° C. and stirred at 60° C. for 1 h. The reaction mixture was cooled to 0° C., treated with sodium cyanoborohydride (0.0106 g, 0.169 mmol), warmed to RT and stirred for at RT 15 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in methanol (0.50 mL), treated with sodium cyanoborohydride (0.00532 g, 0.0847 mmol), and stirred at 60° C. for 3 h. The reaction mixture was diluted with acetonitrile, methanol and a few drops of water and purified via preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (11.9 mg, 40%). LCMS calculated for C35H35F2N6O6S (M+H)+: m/z=705.2. found: 705.2.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. temperaturewarmed to RT
  3. stirringstirred for at RT 15 h
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. dissolutionthe residue was dissolved in methanol (0.50 mL)
  6. stirringstirred at 60° C. for 3 h
  7. custompurified via preparative LCMS (XBridge C18 column
  8. washeluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-2f25e1a2938044008543d38065eb0436
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

Loading…