Melanin-concentrating hormone → 1-Bromo-4-[2-(4-chlorophenyl)-1-propylpent-4-en-1-yl]benzene

HRID 2427797Notes

Reaction equation

HRID 2427797 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:18][CH2:19][CH3:20])[CH:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)O)=[CH:4][CH:3]=1.[CH3:21][CH:22](C1NC(=O)C(CCSC)NC(=O)C(NC(C(NC(C(NC(C(NC(C(N)CC(O)=O)=O)C(O)C)=O)CCSC)=O)CCCNC(N)=N)=O)CSSCC(C(NC(C(NC(C(NC(C(O)=O)C(C)C)=O)CCC(O)=O)=O)CC2C3C(=CC=CC=3)NC=2)=O)NC(=O)C2N(CCC2)C(=O)C(CCCNC(N)=N)NC(=O)C(CC2C=CC(O)=CC=2)NC(=O)C(C(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)CNC1=O)[CH3:23]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:18][CH2:19][CH3:20])[CH:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH2:23][CH:22]=[CH2:21])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 16167454Melanin-concentrating hormoneHCID 670164322-(4-Bromophenyl)-1-(4-chlorophenyl)pentan-1-ol

Product 1

HCID 670168371-Bromo-4-[2-(4-chlorophenyl)-1-propylpent-4-en-1-yl]benzene

Procedure

The title compound was prepared from the intermediate from Step D using the conditions described in INTERMEDIATE 1, Step D. The title compound is obtained as a 2.1:1 mixture of diastereomers. 1H NMR for major diastereomer (500 MHz, CDCl3): δ 7.44 (d, J=8.5 Hz, 2H); 7.28 (d, J=8.3 Hz, 2H); 7.05 (d, J=8.2 Hz, 2H); 7.02 (d, J=8.4 Hz, 2H); 5.46-5.35 (m, 1H); 4.82-4.71 (m, 2H); 2.77-2.62 (m, 2H); 2.14-2.02 (m, 2H); 1.35-1.25 (m, 2H); 1.05-0.89 (m, 2H); 0.67 (t, J=7.3 Hz, 3H). LC1 4.66 min. Not ionized

Sources & evidence

ORD record
ord-ab78f8be9e9547e4b6640e5d72d8b01c
Source dataset
uspto-grants-2011_06
Patent number
US07968589B2

Reaction notes

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