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Triethylamine → N-[4-(2,4,6-Trimethylphenyl)-2-thiazolyl]-1-tert-butoxycarbonyl-indoline-2-carboxamide

HRID 2082407
Notes
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Reaction equation

HRID 2082407 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH:9]1[C:17](O)=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.Br.[NH2:55][C:56]1[S:57][CH:58]=[C:59]([C:61]2[C:66]([CH3:67])=[CH:65][C:64]([CH3:68])=[CH:63][C:62]=2[CH3:69])[N:60]=1>CN(C)C=O>[CH3:67][C:66]1[CH:65]=[C:64]([CH3:68])[CH:63]=[C:62]([CH3:69])[C:61]=1[C:59]1[N:60]=[C:56]([NH:55][C:17]([CH:9]2[CH2:10][C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])=[O:18])[S:57][CH:58]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2794663Indoline-2-carboxylic acid, N-BOC protectedHCID 168963004-Mesitylthiazol-2-amine hydrobromide

Product 1

HCID 21249482N-[4-(2,4,6-Trimethylphenyl)-2-thiazolyl]-1-tert-butoxycarbonyl-indoline-2-carboxamide
Yield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

21 g of 1-tert-butoxycarbonyl-indoline-2-carboxylic acid, then 35.2 g of 1-benzotriazolyl-oxytris (dimethylamino)phosphonium hexafluorophosphate (BOP) and the 24.2 g of triethylamine are added successively to a solution of 23.5 g of 2-amino-4-(2,4,6-trimethylphenyl)thiazole hydrobromide in 250 ml of dimethylformamide. The reaction mixture is stirred at ambient temperature for 12 h. The solvent is then evaporated under reduced pressure and 150 ml of ethyl acetate are poured onto the residue. The organic solution is washed with a saturated aqueous NaCl solution and dried over anhydrous magnesium sulphate. The solid obtained after evaporation of the solvent is washed with diisopropyl ether. Yield: 95%.

Workup

  1. customThe solvent is then evaporated under reduced pressure and 150 ml of ethyl acetate
  2. additionare poured onto the residue
  3. washThe organic solution is washed with a saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customThe solid obtained
  6. customafter evaporation of the solvent
  7. washis washed with diisopropyl ether

Sources & evidence

ORD record
ord-cb90ce2c511340eebdd2aa342fbc8693
Source dataset
uspto-grants-1993_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05189049

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes