Dichloromethane → HCID 16747123, compound

HRID 1009146Notes

Reaction equation

HRID 1009146 reaction equation
Cl.Cl.[NH2:3][C@@H:4]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=1)[C@H:5]([OH:25])[CH2:6][NH:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=2)[NH:11][C:10]([CH3:24])([CH3:23])[CH2:9]1.C(N(C(C)C)C(C)C)C.C(Cl)Cl.N1([C:51](=[O:53])[CH3:52])C=CN=C1>>[CH3:23][C:10]1([CH3:24])[CH2:9][C@H:8]([NH:7][CH2:6][C@@H:5]([OH:25])[C@@H:4]([NH:3][C:51](=[O:53])[CH3:52])[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][C:19]([CH3:22])([CH3:20])[CH3:21])[CH:16]=2)[NH:11]1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 81531DiisopropylethylamineHCID 67306065(2R,3S)-3-amino-1-((S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-ylamino)-4-(3-fluorophenyl)butan-2-ol dihydrochloride

Product 1

HCID 16747123HCID 16747123, compound

Procedure

To a solution of (2R,3S)-3-amino-1-((S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-ylamino)-4-(3-fluorophenyl)butan-2-ol dihydrochloride (0.104 g, 0.379 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.396 ml, 2.27 mmol) in DCM (1.52 ml, 0.379 mmol) was added 1-(1H-imidazol-1-yl)ethanone (0.0396 g, 0.360 mmol) in one portion. The resulting solution was stirred over the weekend. The crude mixture was concentrated and purified with the HPLC. Due to insufficient purity, the title compound was free based and purified with the ISCO MPLC. MS m/z: 470 (M+1).

Workup

  1. concentrationThe crude mixture was concentrated
  2. custompurified with the HPLC
  3. custompurified with the ISCO MPLC

Sources & evidence

ORD record
ord-fe13ee38e4a74bb0ad59b75f7298a4af
Source dataset
uspto-grants-2011_07
Patent number
US07973047B2

Reaction notes

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