1-(2-Amino-4-fluorophenyl)-4-chloro-1-butanone → HCID 44378001, compound

HRID 1266123Notes

Reaction equation

HRID 1266123 reaction equation
[CH:1]1[C:10]2[C@H:11]3[CH2:16][NH:15][CH2:14][CH2:13][C@H:12]3[N:8]3[C:9]=2[C:4]([CH2:5][CH2:6][CH2:7]3)=[CH:3][CH: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>>[CH:1]1[C:10]2[C@H:11]3[CH2:16][N:15]([CH2:28][CH2:27][CH2:26][C:25]([C:19]4[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:18]=4[NH2:17])=[O:30])[CH2:14][CH2:13][C@H:12]3[N:8]3[C:9]=2[C:4]([CH2:5][CH2:6][CH2:7]3)=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 220217371-(2-Amino-4-fluorophenyl)-4-chloro-1-butanoneHCID 69433998(+/-)-cis-5,6,7a,8,9,10,11, 11a-octahydro-4H-pyrido[3',4':4,5]pyrrolo[3,2,1-ij]quinoline

Product 1

HCID 44378001HCID 44378001, compound

Procedure

The title compound was prepared by the method of Example 402 as a red oil (99 mg, 54%) from (±)-cis-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (100 mg, 0.47 mmol) and 1-(2-amino-4-fluorophenyl)-4-chloro-1-butanone (152 mg, 0.70 mmol). 1H NMR (CDCl3, 300 MHz) δ1.95-2.15 (m, 7H), 2.37-2.57 (m, 5H), 2.67-2.85 (m, 3H), 2.90-3.05 (m, 3H), 3.24-3.33 (m, 2H), 6.27-6.39 (m, 2H), 6.41-6.50 (br, 2H), 6.64 (t, J=7.3 Hz, 1H), 6.85-6.94 (m, 2H), 7.77 (dd, J=9.2, 6.6 Hz, 1H) ppm.

Sources & evidence

ORD record
ord-099e89e3228e4f558b845763e7f8b223
Source dataset
uspto-grants-2003_04
Patent number
US06548493B1

Reaction notes

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