Diisopropylethylamine → HCID 86709530, compound

HRID 1848547Notes

Reaction equation

HRID 1848547 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:16])[CH2:4][CH2:3]1.[CH3:17][C:18]1[C:26]2[CH2:25][O:24][C:23](=[O:27])[C:22]=2[CH:21]=[CH:20][C:19]=1[C@H:28]1[CH2:30][O:29]1.CCN(C(C)C)C(C)C>C(O)C>[OH:29][C@H:28]([C:19]1[C:18]([CH3:17])=[C:26]2[C:22](=[CH:21][CH:20]=1)[C:23](=[O:27])[O:24][CH2:25]2)[CH2:30][N:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:16])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22380589Spiro[indole-3,4'-piperidin]-2(1H)-one--hydrogen chloride (1/1)HCID 59568665(S)-4-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-one

Product 1

HCID 86709530HCID 86709530, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Commercially available spiro[indoline-3,4′-piperidin]-2-one hydrochloride (500 mg, 2.10 mmol) was combined with 4-methyl-5-[(2S)-oxiran-2-yl]-2-benzofuran-1(3H)-one (I-4A) (398 mg, 2.10 mmol) and DIEA (439 μL, 2.51 mmol) in ethanol (7 mL) and heated at 80° C. for 3 h. The reaction mixture was concentrated and purified by MPLC eluting first with 30% ethyl acetate/hexanes and then with 10% methanol/DCM to afford the title compound which was a mixture of regioisomers. MS-ESI (m/z): 393 (M+1)+;

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by MPLC
  3. washeluting first with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e693d60c76834cf1b2a1ab1546f02c15
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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