2-Morpholinoethylamine → HCID 21087771, compound

HRID 349281Notes

Reaction equation

HRID 349281 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[F:10][C:11]([F:51])([F:50])[C:12]1[CH:13]=[C:14]([CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:45]=1)[CH2:15][N:16]1[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:19]([C:27]([C:29]2[C:30]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[Cl:42])=[N:31][O:32][C:33]=2[CH:34]=O)=[O:28])[N:18]=[N:17]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[F:50][C:11]([F:10])([F:51])[C:12]1[CH:13]=[C:14]([CH:43]=[C:44]([C:46]([F:47])([F:48])[F:49])[CH:45]=1)[CH2:15][N:16]1[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:19]([C:27]([C:29]2[C:30]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[Cl:42])=[N:31][O:32][C:33]=2[CH2:34][NH:1][CH2:2][CH2:3][N:4]2[CH2:9][CH2:8][O:7][CH2:6][CH2:5]2)=[O:28])[N:18]=[N:17]1

Participants

5

Reactant 3

HCID 4082852-MorpholinoethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86601235HCID 86601235, compound

Product 1

HCID 21087771HCID 21087771, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Add 4-(2-aminoethyl)-morpholine (129 mg, 0.992 mmol) to a solution of 4-[1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazole-4-carbonyl]-3-(2-chloro-phenyl)-isoxazole-5-carbaldehyde (150 mg, 0.248 mmol) in 1,2-dichloroethane (2.5 mL). Then add NaBH(OAc)3 (157 mg, 0.744 mmol) and allow the mixture to stir at RT. After 3 h., quench the reaction with water and extract with EtOAc (2×50 mL). Dry the organic layer over MgSO4, filter, and concentrate in vacuo. Purify the residue by flash chromatography on silica gel to provide the title compound (61% yield) as a brown oil. MS (ES) 720.1 (M++1); TLC Rf=0.1 (EtOAc).

Workup

  1. customquench
  2. customthe reaction with water
  3. extractionextract with EtOAc (2×50 mL)
  4. dry with materialDry the organic layer over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the residue by flash chromatography on silica gel

Sources & evidence

ORD record
ord-3a94dafb598647ceb91e2cbc961ee3c8
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

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