Dichloromethane methanol → HCID 118519577, compound

HRID 1050213Notes

Reaction equation

HRID 1050213 reaction equation
[NH2:1][CH2:2][C@H:3]1[C@H:11]2[N:6]([C:7]3[CH:15]=[CH:14][C:13]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][C:17]4=[O:22])=[CH:12][C:8]=3[O:9][CH2:10]2)[C:5](=[O:23])[O:4]1.[Cl:24][C:25]1[S:26][C:27]([N:30]=[C:31]=[O:32])=[CH:28][CH:29]=1.C(Cl)Cl.CO>C(Cl)Cl>[Cl:24][C:25]1[S:26][C:27]([NH:30][C:31]([NH:1][CH2:2][C@H:3]2[C@H:11]3[N:6]([C:7]4[CH:15]=[CH:14][C:13]([N:16]5[CH2:21][CH2:20][O:19][CH2:18][C:17]5=[O:22])=[CH:12][C:8]=4[O:9][CH2:10]3)[C:5](=[O:23])[O:4]2)=[O:32])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 21226129Dichloromethane methanolHCID 233337682-Chloro-thiophene-5-isocyanateHCID 90295505HCID 90295505, compound

Product 1

HCID 118519577HCID 118519577, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound (3S,3 aS)-3-aminomethyl-7-(3-oxomorpholin-4-yl)-3a,4-dihydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-1(3H)-one (the product of step (e) in Example 1) (98 mg, 0.307 mmol) was dissolved in 10 ml DCM. TEA (46 mg, 0.45 mmol) was added and the reaction mixture was flushed with Ar. 2-chloro-5-thienylisocyanate (58.8 mg, 0.368 mmol) was added on ice bath, and the resulting mixture was agitated at room temperature overnight. TLC (DCM/MeOH=10/1) was employed to monitor the reaction. After the reaction completed, low boiling point solvent was evaporated under reduced pressure. Column chromatography (DCM/MeOH=100/1) afforded 87 mg white solid, yield: 59.2%.

Workup

  1. customthe reaction mixture was flushed with Ar
  2. customthe reaction
  3. customlow boiling point solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9eac9c22453b46428370c1d680fda6f6
Source dataset
uspto-grants-2016_07
Patent number
US09382265B2

Reaction notes

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