Diisopropylethylamine → HCID 178433747, compound

HRID 2401804Notes

Reaction equation

HRID 2401804 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:17]3[C:18]([CH3:28])=[N:19][N:20]4[CH:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][C:21]=34)[S:10][C:11]=2[C:12]2[NH:16][CH:15]=[N:14][N:13]=2)=[CH:4][CH:3]=1.[N:31]1[CH:36]=[CH:35][N:34]=[CH:33][C:32]=1[C:37](Cl)=[O:38].C(N(CC)C(C)C)(C)C>C(Cl)Cl.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:17]3[C:18]([CH3:28])=[N:19][N:20]4[CH:25]=[CH:24][C:23]([CH2:26][NH:27][C:37]([C:32]5[CH:33]=[N:34][CH:35]=[CH:36][N:31]=5)=[O:38])=[CH:22][C:21]=34)[S:10][C:11]=2[C:12]2[NH:16][CH:15]=[N:14][N:13]=2)=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 88279Pyrazinecarbonyl chloride2×HCID 178433745HCID 178433745, compound

Product 1

HCID 178433747HCID 178433747, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-{3-[4-(4-chlorobenzyl)-5-(4H-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]-2-methylpyrazolo[1,5-a]pyridin-5-yl}methanamine (0.0222 g, 0.0491), pyrazine-2-carboxylic acid chloride (8.0 mg, 0.056 mmol) and N,N-diisopropylethylamine (10 mg, 0.08 mmol) in dry Methylene chloride (5.0 mL) in dry N,N-dimethylformamide (1.0 mL) was sonicated for 2 min. The mixture was stirred at rt for 22 hours. N,N-diisopropylethylamine (13 mg, 0.10 mmol) and pyrazine-2-carboxylic acid chloride (9.11 mg, 0.0639 mmol) were added and the mixture was stirred at rt for 3 days. The mixture was quenched with water, then extracted with DCM (3×30 mL). The combined DCM solutions were washed with water, brine, dried over Na2SO4, filtered, and evaporated to give a crude product (80 mg). The crude product was purified by HPLC to give a solid product (0.0007 g, yield 3%). LCMS: (AA) ES+ 542, 544. 1H NMR (400 MHz, d6-DMSO) δ: 9.72-9.74 (d, J=6.53 Hz, 1H), 9.23 (s, 1H), 8.87 (s, 1H), 8.75 (s, 1H), 8.67-8.69 (d, J=6.53 Hz, 1H), 8.63 (s, 1H), 8.22 (s, 1H), 7.24-7.30 (m, 4H), 7.03-7.05 (d, J=7.28 Hz, 1H), 4.62-4.64 (d, J=6.78 Hz, 2H), 4.47 (s, 2H), 2.63 (s, 3H).

Workup

  1. customwas sonicated for 2 min
  2. stirringthe mixture was stirred at rt for 3 days
  3. customThe mixture was quenched with water
  4. extractionextracted with DCM (3×30 mL)
  5. washThe combined DCM solutions were washed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give a crude product (80 mg)
  10. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-57f3fc757c34450c9b18a2c034dadaa9
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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