7-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone → (S)-Ethyl 3-methyl-2-(2-(2-(4-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-7-yloxy)butyl)piperazin-1-yl)phenoxy)acetamido)butanoate

HRID 887060Notes

Reaction equation

HRID 887060 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:17])[NH:14]2)=[CH:9][CH:8]=1.[CH2:18]([O:20][C:21](=[O:50])[C@@H:22]([NH:26][C:27](=[O:49])[CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N:36]1[CH2:41][CH2:40][N:39](C(OC(C)(C)C)=O)[CH2:38][CH2:37]1)[CH:23]([CH3:25])[CH3:24])[CH3:19]>>[CH3:25][CH:23]([CH3:24])[C@H:22]([NH:26][C:27](=[O:49])[CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N:36]1[CH2:37][CH2:38][N:39]([CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][C:13](=[O:17])[NH:14]3)=[CH:9][CH:8]=2)[CH2:40][CH2:41]1)[C:21]([O:20][CH2:18][CH3:19])=[O:50]

Participants

3

Reactant 2

HCID 105420647-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinoneHCID 86625001(S)-tert-Butyl 4-(2-(2-(1-ethoxy-3-methyl-1-oxobutan-2-ylamino)-2-oxoethoxy)phenyl)-piperazine-1-carboxylate

Product 1

HCID 25142507(S)-Ethyl 3-methyl-2-(2-(2-(4-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-7-yloxy)butyl)piperazin-1-yl)phenoxy)acetamido)butanoate

Procedure

(S)-Ethyl 3-methyl-2-(2-(2-(4-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-7-yloxy)butyl)piperazin-1-yl)phenoxy)acetamido)butanoate (14b) (Scheme 2) was synthesized from the compounds 3 and 13b by following the protocol described for the compound 14a (Example 15). Colorless oil, 0.27 g (58%). 1H NMR (400 MHz, CDCl3): δ 0.83 (d, J=7.0 Hz, 3H); 0.90 (d, J=7.0 Hz, 3H); 1.24 (t, J=7.2 Hz, 3H); 1.60-1.69 (m, 2H); 1.74-1.79 (m, 2H); 2.13 (quintet, J=6.4 Hz, 1H); 2.43 (t, J=7.2 Hz, 2H); 2.55 (t, J=7.2 Hz, 2H); 2.65 (broad s, 4H); 2.82 (t, J=7.2 Hz, 2H); 3.01-3.13 (m, 4H); 3.90 (t, J=6.0 Hz, 2H); 4.05 (q, J=7.2 Hz, 2H); 4.53-4.56 (m, 1H); 4.60 (two s, 2H); 6.39 (d, J=2.4 Hz, 1H); 6.45-6.47 (m, 1H); 6.84-6.87 (m, 1H); 6.92-6.95 (m, 3H); 7.56 (d, J=9.2 Hz, 1H); 9.46 (broad s, 2H). MS (ESI): m/z=581.30 (M+H+).

Sources & evidence

ORD record
ord-2c1982a451c34bceb4cd9df38796ef3c
Source dataset
uspto-grants-2012_08
Patent number
US08247420B2

Reaction notes

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