Methylamine → HCID 69153295, compound

HRID 969261Notes

Reaction equation

HRID 969261 reaction equation
[CH2:1]1[C@@H:5]2[CH2:6][O:7][C:8]3[CH:15]=[CH:14][C:13]([C:16](Cl)=[O:17])=[CH:12][C:9]=3[C:10](=[O:11])[N:4]2[CH2:3][CH2:2]1.[CH3:19][NH2:20]>ClCCl.O1CCCC1>[CH3:19][NH:20][C:16]([C:13]1[CH:14]=[CH:15][C:8]2[O:7][CH2:6][C@H:5]3[CH2:1][CH2:2][CH2:3][N:4]3[C:10](=[O:11])[C:9]=2[CH:12]=1)=[O:17]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 87676305HCID 87676305, compound

Product 1

HCID 69153295HCID 69153295, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]benzoxazepine-5-one-7-carboxylic acid chloride (0.330 g; 1.24 mmol), prepared as described in Example 17A, starting from the material described in Example 3I, in dichloromethane (3 ml) was added dropwise to a stirred 10% solution of methylamine in tetrahydrofuran. The mixture was stirred at room temperature for a further 1 h and then evaporated to dryness under reduced pressure. The residue was taken up in dichloromethane (20 mL) and washed with 0.5M HCl (2×20 mL). The dichloromethane layer was dried (MgSO4) and solvent evaporated under reduced pressure. Recrystallisation of the crude product from ethylacetate/diethylether gave the title compound (0.262 g) as a white solid. M.p. 186-189° C.; EIMS: m/z=261.0 [M+H]+

Workup

  1. customevaporated to dryness under reduced pressure
  2. washwashed with 0.5M HCl (2×20 mL)
  3. dry with materialThe dichloromethane layer was dried (MgSO4) and solvent
  4. customevaporated under reduced pressure
  5. customRecrystallisation of the crude product from ethylacetate/diethylether

Sources & evidence

ORD record
ord-e65820621e494f139cc5bf8913f23255
Source dataset
uspto-grants-2007_12
Patent number
US07307073B2

Reaction notes

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