Ethyl isocyanate → HCID 86691739, compound

HRID 1426952Notes

Reaction equation

HRID 1426952 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:22](=[CH:23][CH:24]=1)[O:21][CH2:20][CH2:19][NH:18][CH2:17][C:16]1=[C:25]3[N:26]=[C:10]([CH:11]=[CH:12][N:13]3[N:14]=[CH:15]1)[N:9]1[C@@H:5]2[CH2:6][CH2:7][CH2:8]1.[N:27]([CH2:30][CH3:31])=[C:28]=[O:29].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:30]([NH:27][C:28]([N:18]1[CH2:17][C:16]2=[C:25]3[N:26]=[C:10]([CH:11]=[CH:12][N:13]3[N:14]=[CH:15]2)[N:9]2[C@H:5]([CH2:6][CH2:7][CH2:8]2)[C:4]2[C:22](=[CH:23][CH:24]=[C:2]([F:1])[CH:3]=2)[O:21][CH2:20][CH2:19]1)=[O:29])[CH3:31]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 81531DiisopropylethylamineHCID 70168839HCID 70168839, compound

Product 1

HCID 86691739HCID 86691739, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a DCM (0.5 mL) solution of (6R)-9-fluoro-13-oxa-2,16,20,21,24-pentaazapentacyclo[16.5.2.02,6.07,12.021,25]pentacosa-1(24),7,9,11,18(25),19,22-heptaene (Example 21, 5.5 mg, 0.016 mmol) was added isocyanatoethane (1.5 mg, 0.022 mmol), followed by DIEA (1.9 μL, 0.011 mmol). After stirring at ambient temperature overnight the reaction was concentrated and purified by reverse-phase column chromatography, eluting with 0-80% acetonitrile/H2O to afford the title compound (3.3 mg, 50% yield). MS (apci) m/z=425.4 (M+H).

Workup

  1. concentrationwas concentrated
  2. custompurified by reverse-phase column chromatography
  3. washeluting with 0-80% acetonitrile/H2O

Sources & evidence

ORD record
ord-30fe75b9df1e4be2a754e0094634fad8
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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