Methyl 5-amino-2-bromobenzoate → N-[4-({7-[4-(TRIFLUOROMETHOXY)PHENYL]-1,2,3,4-TETRAHYDRONAPHTHALEN-1-YL}METHYL)BENZOYL]-beta-ALANINE
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[CH:19]=O.Br[C:22]1[CH:29]=CC(Br)=C[C:23]=1C=O.NC1C=CC(Br)=CC=1C(OC)=O.NC1C=CC(Br)=C(C=1)C(OC)=O.BrC1(OC(F)(F)F)C=CC(C2C=CC=CC=2)=CC1C[CH2:69][C:70]1[CH:87]=[CH:86][C:73]([C:74]([NH:76][CH2:77][CH2:78][C:79]([O:81]C(C)(C)C)=[O:80])=[O:75])=[CH:72][CH:71]=1>>[F:18][C:15]([F:17])([F:16])[O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[C:3]3[C:2]([CH2:23][CH2:22][CH2:29][CH:19]3[CH2:69][C:70]3[CH:87]=[CH:86][C:73]([C:74]([NH:76][CH2:77][CH2:78][C:79]([OH:81])=[O:80])=[O:75])=[CH:72][CH:71]=3)=[CH:7][CH:6]=2)=[CH:9][CH:10]=1Participants
6
Reactant 5
Product 1
Procedure
The compounds in TABLE 1 were prepared using the chemistry described in EXAMPLES 1, 4, 5 and 6 or with following modifications: 1) EXAMPLES 47 to 50 (where R1=R21) were prepared as described in EXAMPLE 1 substituting 4-bromo-4′-(trifluoromethoxy)biphenyl-3-carbaldehyde with 2,5-dibromobenzaldehyde; 2) EXAMPLES 117 to 133 were prepared as described in EXAMPLE 1 substituting methyl 2-amino-5-bromobenzoate with methyl 5-amino-2-bromobenzoate; 3) EXAMPLES 111 to 113 were prepared from the intermediate from EXAMPLE 1 Step H using the procedure described in EXAMPLE 42A/42B.
Workup
- customThe compounds in TABLE 1 were prepared
- custom1) EXAMPLES 47 to 50 (where R1=R21) were prepared
- custom2) EXAMPLES 117 to 133 were prepared
Sources & evidence
- ORD record
- ord-efd1db6d98fb406784f43ff5b9d13ec2
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318760B2
Reaction notes
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