Isobutyl chloroformate → HCID 67500007, compound
Reaction equation
[CH3:1][S:2][CH2:3][C:4]([OH:6])=O.C(N(C(C)C)C(C)C)C.ClC(OCC(C)C)=O.[Cl:24][C:25]1[C:29]([NH:30][CH3:31])=[CH:28][N:27]([C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[N:26]=1>C(Cl)Cl>[Cl:24][C:25]1[C:29]([N:30]([CH3:31])[C:4](=[O:6])[CH2:3][S:2][CH3:1])=[CH:28][N:27]([C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[N:26]=1Participants
Procedure
To an ice cold solution of 2-(methylthio)acetic acid (0.092 g, 0.863 mmol) in DCM (2 mL) was added N-ethyl-N-isopropylpropan-2-amine (0.111 g, 0.863 mmol) followed by isobutyl chloroformate (0.099 ml, 0.767 mmol). Stirring was continued for 10 minutes. Next, the mixed anhydride was added to a solution of 3-chloro-N-methyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine (0.08 g, 0.383 mmol) in DCM (0.66 mL) and the reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was concentrated and purified using reverse phase C-18 column chromatography (0-100% CH3CN/H2O) to yield the title compound as a pale yellow oil (0.075 g, 66%): 1H NMR (400 MHz, CDCl3) δ 8.95 (d, J=2.5 Hz, 1H), 8.62 (dd, J=4.8, 1.4 Hz, 1H), 8.13 (s, 1H), 8.04 (ddd, J=8.3, 2.7, 1.4 Hz, 1H), 7.50-7.43 (m, 1H), 3.26 (s, 3H), 3.12 (s, 2H), 2.24 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 170.00, 148.61, 140.15, 140.03, 135.68, 126.56, 126.42, 125.33, 124.15, 37.16, 34.94, 16.22; ESIMS m/z 297 ([M+H]+).
Workup
- stirringthe reaction mixture was stirred at ambient temperature for 2 hours
- concentrationThe reaction mixture was concentrated
- custompurified
Sources & evidence
- ORD record
- ord-95ec5ea4c5c547a6bfa4f0d5d4d5c893
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815271B2
Reaction notes
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