2-Chloroethyl isocyanate → HCID 86728299, compound

HRID 1776922Notes

Reaction equation

HRID 1776922 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][CH2:42][N:43]=[C:44]=[O:45]>C1COCC1>[Cl:40][CH2:41][CH2:42][NH:43][C:44](=[O:45])[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

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 86728298HCID 86728298, compound

Product 1

HCID 86728299HCID 86728299, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 (100 mg, 0.19 mmol) in THF, 1-chloro-2-isocyanatoethane (60 mg, 0.57 mmol) was added at 80° C. Then the reaction mixture was stirred at room temperature overnight. The mixture was extracted with EtOAc, washed with brine, dried and concentrated to provide 6-(3-(2-chloroethyl)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 (80 mg, yield: 66.5%) without further purification. MS (M+H)+: 628.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-22a058a0c342426baefbad81c0862a4b
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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