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Diisopropylethylamine → HCID 66613368, compound

HRID 1842055
Notes
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Reaction equation

HRID 1842055 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][S:44][CH:43]([C:47]([OH:49])=O)[CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35].[NH2:50][C:51]1[CH:52]=[C:53]2[C:57](=[CH:58][CH:59]=1)[NH:56][N:55]=[C:54]2[C:60]([O:62][CH3:63])=[O:61]>CN(C=O)C>[CH3:63][O:62][C:60]([C:54]1[C:53]2[C:57](=[CH:58][CH:59]=[C:51]([NH:50][C:47]([CH:43]3[S:44][CH2:45][CH2:46][N:41]([C:39]([O:38][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:40])[CH2:42]3)=[O:49])[CH:52]=2)[NH:56][N:55]=1)=[O:61]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27606194-(Tert-butoxycarbonyl)thiomorpholine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 28819013Methyl 5-amino-1H-indazole-3-carboxylate

Product 1

HCID 66613368HCID 66613368, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (1.9 g, 5 mmol) and diisopropyl ethyl amine (DIEA) (2.7 mL) was added to a suspension of 4-(tert-butoxycarbonyl)thiomorpholine-2-carboxylic acid (1.3 g, 5 mmol) in DMF (10 mL) and was stirred at room temperature for 15 minutes. Methyl 5-amino-1H-indazole-3-carboxylate (0.95 g, 5 mmol)) was added to the reaction and was stirred at room temperature for an additional 30 minutes. The reaction was quenched with water (50 mL) and extracted with ethyl acetate (3×20 mL). The extracts were combined, dried using anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product (2.1 g) was progressed to the next step without purification.

Workup

  1. stirringwas stirred at room temperature for an additional 30 minutes
  2. customThe reaction was quenched with water (50 mL)
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product (2.1 g) was progressed to the next step without purification

Sources & evidence

ORD record
ord-050bb8362c594cab9053cd6c1e049907
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946216B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes