3-Methoxypropylamine → HCID 68864093, compound

HRID 1725920Notes

Reaction equation

HRID 1725920 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].O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.[CH3:58][O:59][CH2:60][CH2:61][CH2:62][NH2:63]>ClCCl.CN(C)C1C=CN=CC=1.O>[CH3:58][O:59][CH2:60][CH2:61][CH2:62][NH:63][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:17])=[O:18])=[O:22]

Participants

9

Reactant 5

HCID 16723-MethoxypropylamineHCID 79724-Methylmorpholine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68863930HCID 68863930, compound

Product 1

HCID 68864093HCID 68864093, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Example 149B (93.0 mg, 0.241 mmol) in dichloromethane (3.0 mL) was treated with 1-hydroxybenzotriazole hydrate (34 mg, 0.253 mmol) and 4-methylmorpholine (32 μL, 0.297 mmol), stirred at room temperature for 10 minutes, treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (51 mg, 0.266 mmol), 4-dimethylaminopyridine (3 mg, 0.025 mmol), and 1-methoxy-3-aminopropane (37 μL, 0.363 mmol), stirred for 1 hour, heated to 40° C., stirred overnight, treated with 4-dimethylaminopyridine (3 mg, 0.025 mmol) and 4-methylmorpholine (53 μL, 0.482 mmol), heated to 40° C. for 3 days, cooled to room temperature, and treated with distilled water. The aqueous layer was extracted with dichloromethane (2×) and the combined organic phases 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 457 (M+H)+, 479, (M+Na)+; (ESI(−)) m/e 455 (M−H)−.

Workup

  1. stirringstirred for 1 hour
  2. temperatureheated to 40° C.
  3. stirringstirred overnight
  4. temperatureheated to 40° C. for 3 days
  5. temperaturecooled to room temperature
  6. extractionThe aqueous layer was extracted with dichloromethane (2×)
  7. washthe combined organic phases were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b5af0a5d3a4a4cbbad5481dc394bc0b5
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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