HCID 21302475, compound → 1-(2-amino-4-fluorophenyl)-4-[(10R,15S)-4-oxa-1,12-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-5,7,9(16)-trien-12-yl]butan-1-one

HRID 1764923Notes

Reaction equation

HRID 1764923 reaction equation
[CH2:1]1[N:11]2[C:12]3[C:8]([C@@H:9]4[CH2:16][NH:15][CH2:14][CH2:13][C@@H:10]42)=[CH:7][CH:6]=[CH:5][C:4]=3[O:3][CH2:2]1.[NH2:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[C:25](=[O:30])[CH2:26][CH2:27][CH2:28]Cl>>[NH2:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[C:25](=[O:30])[CH2:26][CH2:27][CH2:28][N:15]1[CH2:14][CH2:13][C@@H:10]2[N:11]3[CH2:1][CH2:2][O:3][C:4]4[CH:5]=[CH:6][CH:7]=[C:8]([C:12]3=4)[C@@H:9]2[CH2:16]1

Participants

3

Reactant 2

HCID 21302475HCID 21302475, compoundHCID 220217371-(2-Amino-4-fluorophenyl)-4-chloro-1-butanone

Product 1

HCID 98654631-(2-amino-4-fluorophenyl)-4-[(10R,15S)-4-oxa-1,12-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-5,7,9(16)-trien-12-yl]butan-1-one

Procedure

The title compound was prepared by the method of Example 361 as a red oil (11 mg, 24%) from (±)-cis-1,2,6b,7,8,9,10,10a-octahydro[1,4]oxazino-[2,3,4-hi]pyrido[4,3-b]indole (30 mg, 0.12 mmol) and 1-(2-amino-4-fluorophenyl)-4-chloro-1-butanone (51 mg, 0.24 mmol). 1H NMR (CDCl3, 300 MHz) δ1.87-2.15 (m, 5H), 2.25-2.45 (m, 3H), 2.65-2.79 (m, 2H), 2.86-2.95 (m, 3H), 3.15-3.30 (m, 3H), 4.44 (dd, J=6.9, 2.2 Hz, 2H), 6.26-6.38 (m, 2H), 6.41-6.50 (br-s, 2H), 6.60-6.72 (m, 3H), 7.78 (dd, J=9.1, 6.6 Hz, 1H) ppm.

Sources & evidence

ORD record
ord-c12475c7e6914e6483c0ccb9cd79037c
Source dataset
uspto-grants-2007_06
Patent number
USRE039679E1

Reaction notes

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