Morpholine → HCID 59006936, compound

HRID 1174535Notes

Reaction equation

HRID 1174535 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[C:14]([C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][CH:21]=1)=[N:13][C@H:12]1[C@@H:7]2[CH2:8][O:9][CH2:10][CH2:11]1)[CH3:2].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[NH:60]1[CH2:65][CH2:64][O:63][CH2:62][CH2:61]1>ClCCl>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[C:14]([C:20]1[CH:21]=[CH:22][C:23]([C:24]([N:60]3[CH2:65][CH2:64][O:63][CH2:62][CH2:61]3)=[O:26])=[CH:27][CH:28]=1)=[N:13][C@H:12]1[C@@H:7]2[CH2:8][O:9][CH2:10][CH2:11]1)[CH3:2]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59006941HCID 59006941, compound

Product 1

HCID 59006936HCID 59006936, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1 mmol of 4-((4aR,10aR)-6-Ethoxy-7-methoxy-1,4,4a,10a-tetrahydro-2H-3-oxa-10-aza-phenanthren-9-yl)-benzoic acid, 5 mmol of triethyl amine and 1.1 mmol of O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluoro-phosphate (HBTU) in 20 ml of dichloromethane is stirred for 30 min at RT. After addition of 1.1 mmol of morpholine the suspension is stirred for 60 min at RT. The mixture is concentrated under reduced pressure and the solid residue is purified by column chromatography on SiO2 (n-hexane/ethyl acetate/triethylamine 4/5/1 vol/vol/vol), the main product fraction is separated and concentrated yielding the title compound as grayish solid foam. M.p. 116-120° C. (unsharp, enamel-like shrinking starting at about 61° C.)

Workup

  1. stirringis stirred for 60 min at RT
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customthe solid residue is purified by column chromatography on SiO2 (n-hexane/ethyl acetate/triethylamine 4/5/1 vol/vol/vol)
  4. customthe main product fraction is separated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1e03cba43be044baad0fcce8116426a3
Source dataset
uspto-grants-2010_11
Patent number
US07838521B2

Reaction notes

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