Morpholine → HCID 58882933, compound

HRID 2364145Notes

Reaction equation

HRID 2364145 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]([C:32]1[CH:33]=[C:34]([NH:43][CH2:44][C:45]([OH:47])=O)[C:35]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[N:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[NH:48]1[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1.CCN(CC)CC>CN(C=O)C>[CH2:25]([C:32]1[CH:33]=[C:34]([NH:43][CH2:44][C:45]([N:48]2[CH2:53][CH2:52][O:51][CH2:50][CH2:49]2)=[O:47])[C:35]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[N:36][CH:37]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58882957HCID 58882957, compound

Product 1

HCID 58882933HCID 58882933, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (494 mg, 1.3 mmol) was added via spatula to a solution of N-[5-benzyl-2-(ethoxycarbonyl)pyridin-3-yl]glycine (328 mg, 1.04 mmol), morpholine (0.113 mL, 1.3 mmol) and Et3N (0.18 mL, 1.3 mmol) in DMF (6 mL). After stirring for 45 min at rt, the solvent was removed in vacuo and the resulting material was dissolved in CH2Cl2 and washed with water. The organic layer was dried and concentrated. Purification of the crude material by silica gel chromatography eluting with 0-5% MeOH/CH2Cl2 afforded the product: 1H NMR (CDCl3) δ 8.57 (1H, br), 7.94 (1H, s), 7.23 (3H, m), 7.15 (2H, m), 6.68 (1H, s), 4.46 (2H, q, J=7 Hz), 3.95 (2H, s), 3.90 (2H, d, J=4.2 Hz), 3.68 (6H, br), 3.43 (2H, br), 1.42 (3H, t, J=7 Hz); ES+ MS: 384 (M+H+, 70).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe resulting material was dissolved in CH2Cl2
  3. washwashed with water
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customPurification of the crude material by silica gel chromatography
  7. washeluting with 0-5% MeOH/CH2Cl2
  8. customafforded the product

Sources & evidence

ORD record
ord-0c28eec336184364838facb570b7435a
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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