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Diisopropylethylamine → HCID 23508314, compound

HRID 1883709
Notes
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Reaction equation

HRID 1883709 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([CH2:17][C:18]([OH:20])=O)[CH:14]=[CH:13][C:11]=2[N:12]=1.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.Cl.[NH2:56][C:57]1[CH:58]=[CH:59][C:60]([CH:66]([CH3:73])[CH2:67][C:68]([O:70][CH2:71][CH3:72])=[O:69])=[C:61]2[C:65]=1[CH2:64][CH2:63][CH2:62]2>CN(C)C=O>[C:1]1([CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([CH2:17][C:18]([NH:56][C:57]3[CH:58]=[CH:59][C:60]([CH:66]([CH3:73])[CH2:67][C:68]([O:70][CH2:71][CH3:72])=[O:69])=[C:61]4[C:65]=3[CH2:64][CH2:63][CH2:62]4)=[O:20])[CH:14]=[CH:13][C:11]=2[N:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 235083152-(2-(O-tolylamino)benzo[d]oxazol-6-yl)acetic acidHCID 23508318HCID 23508318, compound

Product 1

HCID 23508314HCID 23508314, compound
Yield 104.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 2-(2-o-tolylamino-benzoxazol-6-yl)acetic acid (0.398 g, Reference Example 2), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.59 g) and diisopropylethylamine (0.24 g) in dimethylformamide was stirred at room temperature for 10 minutes and then treated with a solution of ethyl 3-[7-amino-indan-4-yl]-butanoate hydrochloride (0.4 g, Reference Example 5) in dimethylformamide. After shaking and then allowing to stand at room temperature for 16 hours the reaction mixture was evaporated under high vacuum. The residual red oil was dissolved in ethyl acetate and the solution was washed with 5% aqueous sodium bicarbonate, then with water, then dried over sodium sulfate and then evaporated to give the title compound (0.754 g) as an oil.

Workup

  1. stirringAfter shaking
  2. waitto stand at room temperature for 16 hours
  3. customthe reaction mixture was evaporated under high vacuum
  4. dissolutionThe residual red oil was dissolved in ethyl acetate
  5. washthe solution was washed with 5% aqueous sodium bicarbonate
  6. dry with materialwith water, then dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-37c3801a16e24ff08da15562fe7869e1
Source dataset
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06762199B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes