4-Methylmorpholine → HCID 68864053, compound

HRID 1725944Notes

Reaction equation

HRID 1725944 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[NH:15][S:16]([C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](O)=[O:22])(=[O:18])=[O:17])=[O:4].CN1CCO[CH2:31][CH2:30]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:46]2[N:47]=[CH:48][CH:49]=C[C:45]=2[N:44]=N1.C(N(CCCN)CC)C>CN(C)C=O.O>[CH2:30]([N:47]([CH2:48][CH3:49])[CH2:46][CH2:45][NH:44][C:21]([C:20]1[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=1[S:16]([NH:15][C:6]1[CH:7]=[CH:8][C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]=1[C:3]([O:2][CH3:1])=[O:4])(=[O:18])=[O:17])=[O:22])[CH3:31]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 61011N,N-Diethyl-1,3-propanediamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68863930HCID 68863930, compound

Product 1

HCID 68864053HCID 68864053, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Example 149B (228 mg, 0.592 mmol) in dimethylformamide (3.0 mL) was treated with 4-methylmorpholine (230 μL, 2.07 mmol), cooled to 0° C., treated with O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (450 mg, 1.18 mmol), stirred for 1 hour, treated with 3-(N,N-diethylamino)propylamine (166 μL, 1.18 mmol), warmed to room temperature, stirred overnight, treated with distilled water, and extracted with ethyl acetate three times. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated. The resulting residue was purified by preparative HPLC to provide the desired product. MS (ESI(+)) m/e 484 (M+H)+; (ESI(−)) m/e 482 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.36 (s, 1H), 9.21 (br s, 1H), 9.11 (t, 1H), 8.04 (d, 1H), 7.94 (dd, 1H), 7.79-7.68 (m, 4H), 7.62 (d, 1H), 7.60-7.53 (m, 3H), 3.81 (s, 3H), 3.67 (m, 2H), 3.26 (m, 6H), 1.26 (t, 6H).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred overnight
  3. extractionextracted with ethyl acetate three times
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-97e54e5a593d421bbcdd3fd7ecc61bae
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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