6-Bromo-3,4-dihydroquinolin-2(1H)-one → (S)-6-(2-(2-amino-3-(4-(trifluoromethyl)phenyl)propylamino)thiazol-5-yl)-3,4-dihydroquinolin-2(1H)-one

HRID 2109707Notes

Reaction equation

HRID 2109707 reaction equation
Br[C:2]1[S:6][C:5]([N:7](C(OC(C)(C)C)=O)[CH2:8][C@@H:9]([NH:21]C(=O)OC(C)(C)C)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:44]2[CH:45]=[C:46]3[C:51](=[CH:52][CH:53]=2)[NH:50][C:49](=[O:54])[CH2:48][CH2:47]3)O1.BrC1C=C2C(=CC=1)NC(=O)CC2>>[NH2:21][C@@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:16]=1)[CH2:8][NH:7][C:5]1[S:6][C:2]([C:44]2[CH:45]=[C:46]3[C:51](=[CH:52][CH:53]=2)[NH:50][C:49](=[O:54])[CH2:48][CH2:47]3)=[CH:3][N:4]=1

Participants

4

Reactant 3

HCID 143732816-Bromo-3,4-dihydroquinolin-2(1H)-oneHCID 57634226(S)-tert-butyl 1-(N-(5-bromothiazol-2-yl)-tert-butoxylcarbonylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamateHCID 591171873,4-Dihydro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2(1H)-one

Product 1

HCID 23654066(S)-6-(2-(2-amino-3-(4-(trifluoromethyl)phenyl)propylamino)thiazol-5-yl)-3,4-dihydroquinolin-2(1H)-one

Procedure

The title compound was synthesized using a procedure similar to that shown in Scheme 1 with a coupling reaction between (S)-tert-butyl 1-(N-(5-bromothiazol-2-yl)-tert-butoxylcarbonylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate as shown in Scheme 10 and 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one, which was prepared from commercially available 6-bromo-3,4-dihydroquinolin-2(1H)-one in a similar manner to the procedure shown in Scheme 1. MS m/z: 447 (M+1). 1H NMR (400 MHz, CD3OD): δ ppm 2.55-2.60 (m, 2H), 2.97 (t, J=7.63 Hz, 2H), 3.09 (dd, J=14.97, 7.34 Hz, 2H), 3.52 (d, J=6.85 Hz, 1H), 3.62 (d, J=3.72 Hz, 1H), 3.70 (m, 1H), 6.86 (d, J=8.22 Hz, 1H), 7.23-7.34 (m, 3H), 7.53 (d, J=8.02 Hz, 2H), 7.69 (d, J=8.02 Hz, 2H).

Sources & evidence

ORD record
ord-b8c31239ce8f4fdb999bb444cd2d77a2
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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