Diethyl Ether → HCID 52919831, compound

HRID 872688Notes

Reaction equation

HRID 872688 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:14]=[CH:13][N:12]([CH2:15][C@@H:16]([NH:18][C:19]([C:21]3[N:22]=[C:23](C(OCC)=O)[S:24][CH:25]=3)=[O:20])[CH3:17])[N:11]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH3:31][Mg]Br.CC[O:36][CH2:37][CH3:38].[Cl-].[NH4+]>C1COCC1.C(Cl)Cl.O.CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:14]=[CH:13][N:12]([CH2:15][C@@H:16]([NH:18][C:19]([C:21]3[N:22]=[C:23]([C:37]([OH:36])([CH3:38])[CH3:31])[S:24][CH:25]=3)=[O:20])[CH3:17])[N:11]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

9

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 86670248HCID 86670248, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 52919831HCID 52919831, compoundYield 4.24%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

(S)-ethyl 4-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl-carbamoyl)thiazole-2-carboxylate (0.755 g, 1.701 mmol) was dissolved in dry THF under nitrogen atmosphere. The solution was cooled to −78° C. with acetone-dry icebath. Methylmagnesium bromide, 3 M solution in Et2O (1.134 ml, 3.40 mmol), was added and the reaction mixture was stirred in RT. After the reaction was finished, saturated ammoniumchloride, water and DCM was added. The organic phase was washed with water. The product was purified with Flash-chromatography. Yield 4.24%. 1H-NMR (400 MHz; CDCl3): δ 1.28 (d, 3H), 1.65 (d, 6H), 3.00 (s, 1H), 4.35 (dd, 1H), 4.42 (dd, 1H), 4.58 (m, 1H), 6.62 (d, 7.50 (d, 1H), 7.66 (d, 1H), 7.67 (d, 1H), 7.80 (dd, 1H), 7.91 (d, 1H), 8.00 (s, 1H).

Workup

  1. customdry icebath
  2. washThe organic phase was washed with water
  3. customThe product was purified with Flash-chromatography

Sources & evidence

ORD record
ord-6eeab5fd0fe64896b14f2f5d0088eb0e
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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