Nitrogen → HCID 66928453, compound

HRID 2065023Notes

Reaction equation

N#N.C([O:5][C:6]([C:8]1[S:9][CH:10]=[C:11]([CH2:13][N:14]2[CH:18]=[C:17]([NH:19][C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])=[O:21])[CH:16]=[N:15]2)[N:12]=1)=O)C.CC(C[AlH]CC(C)C)C>C1COCC1.C1(C)C=CC=CC=1>[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][O:22][C:20](=[O:21])[NH:19][C:17]1[CH:16]=[N:15][N:14]([CH2:13][C:11]2[N:12]=[C:8]([CH2:6][OH:5])[S:9][CH:10]=2)[CH:18]=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 4-[4-(2-chloro-benzyloxycarbonylamino)-pyrazol-1-ylmethyl]-thiazole-2-carboxylic acid ethyl ester (912 mg, 2.17 mmol) in THF (20.0 mL) at −78° C. was treated with DiBAL (8.70 mL of a 1M solution in toluene, 8.70 mmol). The reaction mixture was stirred at −78° C. for 1 h, then allowed to reach rt before being quenched with Rochelle's salt (100 mL). The resulting mixture was stirred for 2 h at rt, extracted with EA (2×50 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (19:1 CH2Cl2-MeOH) gave the title compound as a yellow foam. TLC: rf (19:1 CH2Cl2-MeOH)=0.11. LC-MS-conditions 02: tR=0.83 min; [M+H]+=379.04.

Workup

customto reach rt
custombefore being quenched with Rochelle's salt (100 mL)
stirringThe resulting mixture was stirred for 2 h at rt
extractionextracted with EA (2×50 mL)
dry with materialextracts were dried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (19:1 CH2Cl2-MeOH)

Sources & evidence

ORD record: ord-4c3e03c64d924be7b96c6dd4ee00d1ea
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288419B2

Reaction notes

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