Diisopropylethylamine → 8-(Benzyloxy)-5-[(1R)-2-{benzyl[6-(4-phenylbutoxy)hexyl]amino}-1-(tetrahydro-2H-pyran-2-yloxy)ethyl]quinolin-2(1H)-one

HRID 749228Notes

Reaction equation

HRID 749228 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH2:21]Br)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:30]([NH:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(N(C(C)C)CC)(C)C>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH2:21][N:37]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 10914757N-benzyl-6-(4-phenylbutoxy)hexan-1-amineHCID 115833968-(Benzyloxy)-5-[(1R)-2-bromo-1-(tetrahydro-2H-pyran-2-yloxy)ethyl]quinolin-2(1H)-one

Product 1

HCID 115494128-(Benzyloxy)-5-[(1R)-2-{benzyl[6-(4-phenylbutoxy)hexyl]amino}-1-(tetrahydro-2H-pyran-2-yloxy)ethyl]quinolin-2(1H)-oneYield 54.3%

Procedure

8-(Benzyloxy)-5-[(1R)-2-bromo-1-(tetrahydro-2H-pyran-2-yloxy)ethyl]quinolin-2(1H)-one (100 mg), N-benzyl-6-(4-phenylbutoxy)hexan-1-amine (Tetrahedron Letters. 1994, 35, 9375) (112 mg) and diisopropylethylamine (77 μl) were heated in a reacti-vial at 120° C. for 4 h prior to cooling to room temperature. The mixture was purified by chromatography (Hexane-EtOAc 2:1, biotage) afforded the title compound (85 mg). LCMS RT=3.46 min

Workup

  1. customThe mixture was purified by chromatography (Hexane-EtOAc 2:1, biotage)

Sources & evidence

ORD record
ord-5631daf04a634b42b19a40ff5022ede7
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

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