Tetrahydrofuran → 2-Bromo-2-methyl-N-(8-bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)carbamoylpropanamide

HRID 708233Notes

Reaction equation

HRID 708233 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:10][CH2:9][O:8][C:7]3[CH:11]=[C:12]([Br:15])[CH:13]=[CH:14][C:6]=3[C:5]=2[N:16]=1.O1CCCC1.[Br:22][C:23]([CH3:30])([CH3:29])[C:24]([N:26]=[C:27]=[O:28])=[O:25]>>[Br:22][C:23]([CH3:30])([CH3:29])[C:24]([NH:26][C:27](=[O:28])[NH:1][C:2]1[S:3][C:4]2[CH2:10][CH2:9][O:8][C:7]3[CH:11]=[C:12]([Br:15])[CH:13]=[CH:14][C:6]=3[C:5]=2[N:16]=1)=[O:25]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 579002668-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-ylamineHCID 866523302-Bromo-2-methylpropanoyl isocyanate

Product 1

HCID 582038232-Bromo-2-methyl-N-(8-bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)carbamoylpropanamide

Procedure

A mixture of 1250 mg (4.20 mmol) of 2-amino-8-bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepine in tetrahydrofuran (6.75 mL, 83.2 mmol) was mixed with 1.25 g (6.00 mmol, 1.42 eq.) of crude 2-bromo-2-methylpropanoyl isocyanate and stirred for 20 hours. The precipitate was filtered off, washed with ethyl ether and dried on air to give 2-Bromo-2-methyl-N-(8-bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)carbamoylpropanamide. Weight 2.21 g (75%). MS(ESI+): 488.0

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with ethyl ether
  3. customdried on air

Sources & evidence

ORD record
ord-984a09738b01458aa45f1f2fe9cfdb5c
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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