Nitrogen → {1-[2-(1-Hydroxy-ethyl)-thiazol-4-ylmethyl]-1H-pyrazol-4-yl}-carbamic acid 2-chloro-benzyl ester

HRID 2065025Notes

Reaction equation

N#N.[Cl:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[CH2:6][O:7][C:8](=[O:23])[NH:9][C:10]1[CH:11]=[N:12][N:13]([CH2:15][C:16]2[N:17]=[C:18]([CH:21]=[O:22])[S:19][CH:20]=2)[CH:14]=1.[CH3:28][Mg]Br>C1COCC1.[NH4+].[Cl-]>[Cl:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[CH2:6][O:7][C:8](=[O:23])[NH:9][C:10]1[CH:11]=[N:12][N:13]([CH2:15][C:16]2[N:17]=[C:18]([CH:21]([OH:22])[CH3:28])[S:19][CH:20]=2)[CH:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [1-(2-formyl-thiazol-4-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester (155 mg, 0.41 mmol) in THF (4.0 mL) was treated at −78° C. with methylmagnesium bromide (0.41 mL of a 1M solution in THF, 0.41 mmol). The reaction mixture was stirred at −78° C. for 4.5 h then poured in sat. aq. NH4Cl (25 mL) and extracted with EA (2×25 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (90:10 CH2Cl2-MeOH) gave the title compound as a yellow oil. TLC: rf (90:10 CH2Cl2-MeOH)=0.28. LC-MS-conditions 02: tR=0.88 min; [M+H]+=393.11.

Workup

extractionextracted with EA (2×25 mL)
dry with materialextracts were dried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (90:10 CH2Cl2-MeOH)

Sources & evidence

ORD record: ord-d7cb485760844bc291c2642f86afff8e
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288419B2

Reaction notes

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