1-Chloro-N,N-2-trimethylpropenylamine → N-(7-bromo-3-chloro-5',6'-dihydrospiro[chromeno[2,3-c]pyridine-5,4'-[1,3]thiazin]-2'-yl)-4-nitrobenzamide hydrochloride

HRID 931602Notes

Reaction equation

HRID 931602 reaction equation
[Cl:1]C(N(C)C)=C(C)C.[Br:9][C:10]1[CH:11]=[C:12]2[C:22](=[CH:23][CH:24]=1)[O:21][C:15]1[CH:16]=[N:17][C:18]([Cl:20])=[CH:19][C:14]=1[C:13]2([NH:28][C:29]([NH:31][C:32](=[O:42])[C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1)=[S:30])[CH2:25][CH2:26]O>C(Cl)Cl>[ClH:1].[Br:9][C:10]1[CH:11]=[C:12]2[C:13]3([CH2:25][CH2:26][S:30][C:29]([NH:31][C:32](=[O:42])[C:33]4[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=4)=[N:28]3)[C:14]3[CH:19]=[C:18]([Cl:20])[N:17]=[CH:16][C:15]=3[O:21][C:22]2=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 86658374N-((7-bromo-3-chloro-5-(2-hydroxyethyl)-5H-chromeno[2,3-c]pyridin-5-yl)carbamothioyl)-4-nitrobenzamide

Product 1

HCID 86658375N-(7-bromo-3-chloro-5',6'-dihydrospiro[chromeno[2,3-c]pyridine-5,4'-[1,3]thiazin]-2'-yl)-4-nitrobenzamide hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloro-N,N,2-trimethylprop-1-en-1-amine (2.84 ml, 21.28 mmol) was added to a solution of N-((7-bromo-3-chloro-5-(2-hydroxyethyl)-5H-chromeno[2,3-c]pyridin-5-yl)carbamothioyl)-4-nitrobenzamide (12 g, 21.28 mmol) in DCM (200 ml). The reaction mixture was stirred at RT for 8 hours and then concentrated under reduced pressure to 50% of its original volume. A precipitate formed upon cooling which was filtered off, washed with DCM and then dried under reduced pressure to afford N-(7-bromo-3-chloro-5′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,4′-[1,3]thiazin]-2′-yl)-4-nitrobenzamide hydrochloride (10.5 g, 18.03 mmol, 85% yield) as an off white solid.

Workup

  1. concentrationconcentrated under reduced pressure to 50% of its original volume
  2. customA precipitate formed
  3. temperatureupon cooling which
  4. filtrationwas filtered off
  5. washwashed with DCM
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-c836d5ffb25b4e7e9a1aec3caa006931
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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