Triethylamine → HCID 59615715, compound

HRID 1799523Notes

Reaction equation

HRID 1799523 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:15])[S:5][C:6]=1[C:7]#[C:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1.[C:16](N1C=CN=C1)([N:18]1[CH:22]=[CH:21][N:20]=[CH:19]1)=[O:17].C(N(CC)CC)C.CC(OC)(C)C>CN(C=O)C>[CH3:1][C:2]1[N:3]=[C:4]([NH:15][C:16]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)=[O:17])[S:5][C:6]=1[C:7]#[C:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 682631,1'-CarbonyldiimidazoleHCID 59615778HCID 59615778, compound

Product 1

HCID 59615715HCID 59615715, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

As shown in step 2-iii of Scheme 2, compound 1004 (91 mg, 0.423 mmol), 1,1′-carbonyldiimidazole (103 mg, 0.634 mmol), and triethylamine (85.6 mg, 0.845 mmol) were stirred in 2.1 mL of DMF at 60° C. for 2 hours. After this time, MTBE was added and the resulting precipitate collected by filtration to produce N-(4-methyl-5-(pyridin-3-ylethynyl)thiazol-2-yl)-1H-imidazole-1-carboxamide (compound 1005, 120 mg), which was immediately used in subsequent reactions as is.

Workup

  1. filtrationthe resulting precipitate collected by filtration

Sources & evidence

ORD record
ord-48af6891d1f64a83bedb6d1404eaea3f
Source dataset
uspto-grants-2013_01
Patent number
US08344153B2

Reaction notes

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