Diisopropylethylamine → HCID 68651552, compound

HRID 646780Notes

Reaction equation

HRID 646780 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:12]2[CH:13]=[C:14]([CH:18]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[CH:20]=2)[C:15]([OH:17])=O)=[N:6][C:7]=1[C:8]([NH:10][CH3:11])=[O:9].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[NH2:49][C@@H:50]1[C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[CH2:52][CH2:51]1.C(N(C(C)C)CC)(C)C>O.CN(C=O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:12]2[CH:20]=[C:19]([CH:18]=[C:14]([C:15]([NH:49][C@@H:50]3[C:58]4[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=4)[CH2:52][CH2:51]3)=[O:17])[CH:13]=2)[C:21]([O:23][CH3:24])=[O:22])=[N:6][C:7]=1[C:8]([NH:10][CH3:11])=[O:9]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 70000841-Aminoindane, (S)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68650317HCID 68650317, compound

Product 1

HCID 68651552HCID 68651552, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture containing 3-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-5-[(methyloxy)carbonyl]benzoic acid (0.34 g, 1.0 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (0.51 g, 1.6 mmol), (S)-(+)-1-aminoindan (0.17 g, 1.3 mmol), diisopropylethylamine (0.6 mL, 3.4 mmol) and DMF (70 mL) were stirred at room temperature for 12 h. The reaction mixture was diluted with water and extracted 3' with ethyl acetate and 3× with 5% aqueous lithium chloride, and dried over sodium sulfate. Filtration, concentration, and purification by reverse phase HPLC gave the product as a yellow solid (0.41 g, 90% yield). 1H NMR (400 MHz, d6-DMSO): δ 9.09 (d, 1H), 8.91 (s, 1H), 8.83 (d, 1H), 8.75 (t, 1H), 8.70 (t, 1H), 8.45 (t, 1H), 7.73 (br, 2H), 7.28 (d, 2H), 7.24-7.17 (m, 2H), 5.64-5.58 (q, 1H), 3.91 (s, 3H), 3.04-3.00 (m, 1H), 3.00-2.87 (m, 1H), 2.83 (d, 3H), 2.53-2.51 (m, 1H), 2.06-1.96 (m, 1H). MS (EI) for C24H23N5O4: 446 (MH+).

Workup

  1. extractionextracted 3' with ethyl acetate and 3× with 5% aqueous lithium chloride
  2. dry with materialdried over sodium sulfate
  3. filtrationFiltration, concentration, and purification by reverse phase HPLC

Sources & evidence

ORD record
ord-10b7d245cb6c43fbbaa88c8b86f8131b
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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