Triethylamine → HCID 86664612, compound

HRID 537091Notes

Reaction equation

[Br:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[CH2:11][C:12]1(C(O)=O)[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.C([N:30]([CH2:33]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:42])C=CC=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[N:6]([C:7]([CH3:9])([CH3:10])[CH3:8])[N:5]=[CH:4][C:3]=1[CH2:11][C:12]1([N:30]=[C:33]=[O:42])[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[CH2:16][CH2:17]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-((5-bromo-1-tert-butyl-1H-pyrazol-4-yl)methyl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (241 mg, 0.54 mmol) in toluene (10 mL) was added triethylamine (91 μL, 0.65 mmol) and diphenylphosphoryl azide (0.14 mL, 0.65 mmol). The mixture was heated at 120° C. for 3 hours, the reaction was cooled and the volatiles were removed under reduced pressure. The resultant oil was purified by flash chromatography (25 g silica, 7-60% ethyl acetate/heptane gradient) to yield 225 mg of tert-butyl 4-((5-bromo-1-tert-butyl-1H-pyrazol-4-yl)methyl)-4-isocyanatopiperidine-1-carboxylate as a clear oil. +APCI (M+H) 385.1; 1H NMR (400 MHz, CDCl3, δ): 7.40 (s, 1H), 4.03 (br. s., 2H), 2.97 (br. t, J=12.3, 12.3 Hz, 2H), 2.70 (s, 2H), 1.74 (s, 9H), 1.67 (m, 2H), 1.62 (m, 2H), 1.46 (s, 9H).

Workup

temperaturethe reaction was cooled
customthe volatiles were removed under reduced pressure
customThe resultant oil was purified by flash chromatography (25 g silica, 7-60% ethyl acetate/heptane gradient)

Sources & evidence

ORD record: ord-6cf9863479824b7ab1547ba0a942feb3
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859773B2

Reaction notes

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