Hydroxylamine → HCID 19608322, compound

HRID 1602872Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:9]=3[CH:8]([N:18]3[CH2:23][CH2:22][N:21]([C:24](=[O:43])[CH2:25][CH:26]4[CH2:31][CH2:30][N:29]([C:32](=[N:40][C:41]#[N:42])[O:33]C5C=CC=CC=5)[CH2:28][CH2:27]4)[CH2:20][CH2:19]3)[C:5]2=[N:6][CH:7]=1.[NH2:44][OH:45]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:9]=3[CH:8]([N:18]3[CH2:19][CH2:20][N:21]([C:24](=[O:43])[CH2:25][CH:26]4[CH2:27][CH2:28][N:29]([C:32]5[N:40]=[C:41]([NH2:42])[O:45][N:44]=5)[CH2:30][CH2:31]4)[CH2:22][CH2:23]3)[C:5]2=[N:6][CH:7]=1.[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:9]=3[CH:8]([N:18]3[CH2:19][CH2:20][N:21]([C:24](=[O:43])[CH2:25][CH:26]4[CH2:27][CH2:28][N:29]([C:32]5[O:33][N:42]=[C:41]([NH2:44])[N:40]=5)[CH2:30][CH2:31]4)[CH2:22][CH2:23]3)[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Phenyl 4-[2-[4-(3-bromo-8-chloro-6,11-dihydro-5H-benzo[5,6] cyclohepta[1,2-b]pyridin-11-yl)-1-piperazinyl]-2-oxoethyl]-N-cyano-1-piperidine-carboximidate (Step A of Example 8) (1 equivalent) is dissolved in methanol. Hydroxylamine (1 equivalent) is added and the mixture is stirred at 25° C. for 1h. The mixture is evaporated to dryness and chromatographed on silica gel to give the title compounds of Formulas 7.2 ((3-[4-[2-[4-(3-bromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)-1-piperazinyl]-2-oxoethyl]-1-piperidinyl]-5-amino-1,2,4-oxadiazole) and 7.3 ((5-[4-[2-[4-(3-bromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta-[1,2-b]pyridin-11-yl)-1-piperazinyl]-2-oxoethyl]-1-piperidinyl]-3-amino-1,2,4-oxadiazole).

Workup

customThe mixture is evaporated to dryness
customchromatographed on silica gel

Sources & evidence

ORD record: ord-7f873c6ea3f64dd699dd0e4c63d58ade
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05985879

Reaction notes

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