Ethyl isocyanatoacetate → HCID 57947668, compound

HRID 341014Notes

Reaction equation

HRID 341014 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([NH:12][C:13](=[O:35])[O:14][CH2:15][C@@H:16]([N:21]([CH3:34])[C:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=1[Cl:33])=[O:23])[CH2:17][CH2:18][CH2:19][NH2:20])=[CH:5]2.CCN(C(C)C)C(C)C.[N:45]([CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])=[C:46]=[O:47]>C1COCC1>[Cl:33][C:27]1[C:28]([F:32])=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][NH:24][C:22](=[O:23])[N:21]([CH3:34])[C@H:16]([CH2:15][O:14][C:13](=[O:35])[NH:12][C:6]1[N:7]=[CH:8][C:9]2[C:4]([CH:5]=1)=[CH:3][C:2]([F:1])=[CH:11][CH:10]=2)[CH2:17][CH2:18][CH2:19][NH:20][C:46](=[O:47])[NH:45][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50]

Participants

5

Reactant 3

HCID 76283Ethyl isocyanatoacetateHCID 81531DiisopropylethylamineHCID 57947596HCID 57947596, compound

Product 1

HCID 57947668HCID 57947668, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (S)-5-amino-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)pentyl 6-fluoroisoquinolin-3-ylcarbamate (0.40 g, 0.792 mmol), DIEA (0.276 mL, 1.58 mmol) and THF (2 mL), ethyl isocyanatoacetate (0.108 mL, 0.950 mmol) was added. The mixture was refluxed for 30 min, and concentrated. The remaining residue was purified on silica gel column (DCM/MeOH) to give (S)-ethyl 1-(2-chloro-3-fluorophenyl)-5-((6-fluoroisoquinolin-3-ylcarbamoyloxy)methyl)-4-methyl-3,10-dioxo-2,4,9,11-tetraazatridecan-13-oate (0.40 g, 80%). LRMS (M+H+) m/z 635.6.

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed for 30 min
  3. concentrationconcentrated
  4. customThe remaining residue was purified on silica gel column (DCM/MeOH)

Sources & evidence

ORD record
ord-b48f2124cee84b8dbc1bb96814e9fbf1
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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