Benzene, 1-bromo-3-(trifluoromethyl)- → HCID 46194726, compound

HRID 1915197Notes

Reaction equation

HRID 1915197 reaction equation
[CH3:1][C@@H:2]([NH:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=12.BrC1C=C(C(F)(F)F)C=CC=1.C1([C@H](NCC=C)C)C2C(=CC=CC=2)C=CC=1.C(N)C=C>>[C:3]1([C@H:2]([NH:13][CH2:14]/[CH:15]=[CH:16]/[C:17]2[CH:18]=[CH:19][CH:20]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:22]=2)[CH3:1])[C:8]2[C:7](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 156419CinacalcetHCID 67371848HCID 67371848, compound

Product 1

HCID 46194726HCID 46194726, compound

Procedure

U.S. Pat. No. 7,393,967 discloses a process for preparing Cinacalcet via coupling of 3-bromotrifluorotoluene with allylamine (R)—N-(1-(naphthalen-1-yl)ethyl)prop-2-en-1-amine in the presence of a catalyst and at least one base to obtain (R,E)-N-(1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)prop-2-en-1-amine (CNC-ene) and reducing the unsaturated Cinacalcet to obtain Cinacalcet, as depicted in the following Scheme 6:

Sources & evidence

ORD record
ord-14c59dff5d83455998795a0947d5d0eb
Source dataset
uspto-grants-2013_12
Patent number
US08614353B2

Reaction notes

Loading…