ZM 336372 → HCID 22291122, compound

HRID 967863Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[CH3:11][N:12]([CH3:39])[C:13]1[CH:14]=[C:15]([CH:36]=[CH:37][CH:38]=1)[C:16]([NH:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:35])=[C:23]([NH:25][C:26](=[O:34])[C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)[CH:24]=1)=[O:17].C(=O)([O-])[O-].[K+].[K+].CC(N(C)C)=O>O>[CH3:39][N:12]([CH3:11])[C:13]1[CH:14]=[C:15]([CH:36]=[CH:37][CH:38]=1)[C:16]([NH:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:35])=[C:23]([NH:25][C:26](=[O:34])[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:2][CH2:3][CH2:4][N:5]3[CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)=[CH:29][CH:28]=2)[CH:24]=1)=[O:17]

Participants

Conditions

Temperature: 60 °C

Procedure

4-(3-Chloropropyl)morpholine (0.1 g) was added to a stirred mixture of N-[5-(3-dimethylaminobenzamido)-2-methylphenyl]-4-hydroxybenzamide (0.195 g), potassium carbonate (0.21 g) and DMA (5 ml). The mixture was then heated to 60° C. for 36 hours. The mixture was poured into water (150 ml) and the resultant solid was collected, washed with water and with diethyl ether. The product was dried under vacuum. There was thus obtained the title compound (0.203 g) as a colourless solid; NMR Spectrum: (DMSOd6) 1.88 (m, 2H), 2.18 (s, 3H), 2.36 (t, 4H), 2.41 (t, 2H), 2.96 (s, 6H), 3.58 (t, 4H), 4.08 (t, 2H), 6.9 (m, 1H), 7.01 (d, 2H), 7.19 (m, 3H), 7.26 (t, 1H), 7.58 (d, 1H), 7.78 (s, 1H), 7.98 (d, 2H), 9.72 (s, 1H), 10.08 (s, 1H); Mass Spectrum: M+H+ 517.

Workup

customthe resultant solid was collected
washwashed with water and with diethyl ether
customThe product was dried under vacuum

Sources & evidence

ORD record: ord-6462d11ee19046379141010b44bd7911
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06956037B2

Reaction notes

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