Triethylamine → HCID 135546172, compound

HRID 720150Notes

Reaction equation

HRID 720150 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:14](=[O:15])[NH:13][N:12]=[CH:11][C:6]3=[CH:7][NH:8][C:9]([CH:10]=1)=[C:5]23.[CH2:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][N:17]1[CH2:26][C:27]([OH:29])=O.C(N([CH2:35][CH3:36])CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:48]2N=C[CH:51]=[CH:52][C:47]=2N=N1>CN(C)C=O>[CH2:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][N:17]1[CH2:26][C:27]([NH:1][C:2]1[CH:3]=[C:4]2[C:14](=[O:15])[NH:13][N:12]=[CH:11][C:6]3=[C:7]([C:36]4[CH:35]=[CH:51][CH:52]=[CH:47][CH:48]=4)[NH:8][C:9]([CH:10]=1)=[C:5]23)=[O:29]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1514441(3,4-Dihydro-1H-isoquinolin-2-yl)-acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 135774128HCID 135774128, compound

Product 1

HCID 135546172HCID 135546172, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner analogous to that of Example 11, to a stirred solution of 8-amino-1,5-dihydro-6H-[1,2]diazepino[4,5,6-cd] indol-6-one in anhydrous N,N-dimethylformamide (6 mL) was added 3,4-dihydroisoquinolin-2(1H)-ylacetic acid (62 mg, 0.33 mmol) followed by triethylamine (0.14 mL, 0.98 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (372 mg, 0.98 mmol). The reaction was stirred at room temperature for 17 hours. After concentrating, water was added and the precipitated solid was collected by filtration. After preparative HPLC, the title compound (50 mg) was obtained as a yellow powder in 34% yield.

Workup

  1. concentrationAfter concentrating
  2. additionwater was added
  3. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-de9090fcd9ab4c70ae854cbec0550d39
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Reaction notes

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