4-Methylmorpholine → HCID 86755935, compound

HRID 366793Notes

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([O-])[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([OH:56])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]([O-:56])([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

Conditions

Temperature: 20 °C

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 1-oxide (93.3 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 NMM (1 ml) was added. The reaction mixture was stirred at 20° C. for 18 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 chromatographed on silica gel to afford the title compound (107 mg), m.p. 115-118° C.

Workup

extractionthe aqueous phase was then extracted with EtOAc (about 8 times) until no product
washThe EtOAc phase was then washed with aqueous Na2CO3
customchromatographed on silica gel

Sources & evidence

ORD record: ord-845aaa796a7c49cd8740b3eb5c6dbdbd
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130229

Reaction notes

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