1-Chloro-N,N-2-trimethylpropenylamine → N-(7'-bromo-4'-fluoro-2'-methoxy-5,6-dihydrospiro[[1,3]thiazine-4,9'-xanthen]-2-yl)benzamide

HRID 931607Notes

Reaction equation

HRID 931607 reaction equation
ClC(N(C)C)=C(C)C.[Br:9][C:10]1[CH:23]=[C:22]2[C:13]([O:14][C:15]3[C:16]([F:41])=[CH:17][C:18]([O:39][CH3:40])=[CH:19][C:20]=3[C:21]2([NH:27][C:28]([NH:30][C:31](=[O:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[S:29])[CH2:24][CH2:25]O)=[CH:12][CH:11]=1>C(Cl)Cl>[Br:9][C:10]1[CH:23]=[C:22]2[C:13]([O:14][C:15]3[C:16]([F:41])=[CH:17][C:18]([O:39][CH3:40])=[CH:19][C:20]=3[C:21]32[CH2:24][CH2:25][S:29][C:28]([NH:30][C:31](=[O:38])[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[N:27]3)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 86658378N-((7-bromo-4-fluoro-9-(2-hydroxyethyl)-2-methoxy-9H-xanthen-9-yl)carbamothioyl)benzamide

Product 1

HCID 67436735N-(7'-bromo-4'-fluoro-2'-methoxy-5,6-dihydrospiro[[1,3]thiazine-4,9'-xanthen]-2-yl)benzamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloro-N,N,2-trimethylprop-1-en-1-amine (2.012 ml, 15.05 mmol) was added to a solution of N-((7-bromo-4-fluoro-9-(2-hydroxyethyl)-2-methoxy-9H-xanthen-9-yl)carbamothioyl)-benzamide (8 g, 15.05 mmol) in DCM (3 ml). The reaction mixture was stirred at RT for 8 hours. The reaction mixture was quenched with aqueous, saturated sodium carbonate solution and stirred for 10 minutes. The organic layer was separated and concentrated under reduced pressure to afford crude N-(7′-bromo-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]thiazine-4,9′-xanthen]-2-yl)-benzamide (7.7 g, 15.00 mmol, 100% yield).

Workup

  1. customThe reaction mixture was quenched with aqueous, saturated sodium carbonate solution
  2. stirringstirred for 10 minutes
  3. customThe organic layer was separated
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f36b6bc4b4f441bcb09a35ab0d0f5303
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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