4-Methylmorpholine → HCID 44318864, compound

HRID 366794Notes

Reaction equation

HRID 366794 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[CH:6]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:7]3[N:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][N:10]([CH3:11])[C:4]=2[CH:3]=1.[N:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31](O)=[O:32])=[CH:26][CH:25]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C.O>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[CH:6]([N:16]3[CH2:21][CH2:20][N:19]([C:31](=[O:32])[CH2:30][C:27]4[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=4)[CH2:18][CH2:17]3)[C:7]3[N:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][N:10]([CH3:11])[C:4]=2[CH:3]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 342284-Pyridineacetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23289852HCID 23289852, compound

Product 1

HCID 44318864HCID 44318864, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(8-Chloro-6,11-dihydro-6-methyl-5H-pyrido[3,2-c][1]benzazepin-11-yl)-piperazine (100 mg, 0.305 mmol), 4-pyridine-acetic acid (83.6 mg, 0.61 mmol), EDCl (0.116 g, 0.61 mmol) and HOBT (82.4 mg, 0.61 mmol) were dissolved in DMF (2 ml) and stirred for 1 minute, and then NMM (1 ml) was added. The reaction mixture was stirred at 20° C. for 21 hours and then diluted with water (50 ml), and the aqueous phase was then extracted with EtOAc (about 8 times) until no product was visible in the aqueous layer. The EtOAc phase was then washed with aqueous Na2CO3 and evaporated to a residue (152 mg). This was chromatographed on silica gel to afford partially purified title compound (123 mg), which was rechromatographed on silica gel; two fractions, 51.3 and 50.8 mg, were isolated. The latter gave m.p. 83-87° C.

Workup

  1. stirringThe reaction mixture was stirred at 20° C. for 21 hours
  2. extractionthe aqueous phase was then extracted with EtOAc (about 8 times) until no product
  3. washThe EtOAc phase was then washed with aqueous Na2CO3
  4. customevaporated to a residue (152 mg)
  5. customThis was chromatographed on silica gel
  6. customto afford partially
  7. custompurified title compound (123 mg), which
  8. customwas rechromatographed on silica gel
  9. customtwo fractions, 51.3 and 50.8 mg, were isolated
  10. customThe latter gave m.p. 83-87° C.

Sources & evidence

ORD record
ord-f2a80a60fbd74096ae604267b4d0b0fc
Source dataset
uspto-grants-2000_10
Patent number
US06130229

Reaction notes

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