Chloroacetyl isocyanate → HCID 86728300, compound

HRID 1776923Notes

Reaction equation

HRID 1776923 reaction equation
[NH2:1][C:2]1[C:21]([C:22]2[CH:23]=[CH:24][C:25]3[O:38][CH2:37][N:28]4[C:29]5[CH:30]=[CH:31][CH:32]=[C:33]([F:36])[C:34]=5[CH:35]=[C:27]4[C:26]=3[N:39]=2)=[CH:20][C:5]2[C:6]([C:16]([NH:18][CH3:19])=[O:17])=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.[Cl:40][CH2:41][C:42]([N:44]=[C:45]=[O:46])=[O:43]>C1COCC1>[Cl:40][CH2:41][C:42]([NH:44][C:45](=[O:46])[NH:1][C:2]1[C:21]([C:22]2[CH:23]=[CH:24][C:25]3[O:38][CH2:37][N:28]4[C:29]5[CH:30]=[CH:31][CH:32]=[C:33]([F:36])[C:34]=5[CH:35]=[C:27]4[C:26]=3[N:39]=2)=[CH:20][C:5]2[C:6]([C:16]([NH:18][CH3:19])=[O:17])=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1)=[O:43]

Participants

4

Reactant 2

HCID 78209Chloroacetyl isocyanateHCID 86728298HCID 86728298, compound

Product 1

HCID 86728300HCID 86728300, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-amino-5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (200 mg, 0.38 mmol) in THF (15 mL) was added a solution of 2-chloroacetyl isocyanate (100 mg, 0.78 mmol) in THF (1 mL) dropwise under nitrogen. The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, the resulting residue was obtained 6-(3-(2-chloroacetyl)ureido)-5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (203 mg, yield: 81%) without further purification. MS (M+H)+: 642.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f58ba5219209439da7b7206bafcf5ff8
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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