HCID 66602158, compound → HCID 178522452, compound

HRID 2262815Notes

Reaction equation

HRID 2262815 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:12]=[C:11]([S:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([OH:19])=O)[NH:10][N:9]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([N:33]2[CH2:36][CH:35]([NH:37]C(=O)OC(C)(C)C)[CH2:34]2)(=[O:32])=[O:31])=[CH:26][CH:25]=1>>[F:23][C:24]1[CH:25]=[CH:26][C:27]([S:30]([N:33]2[CH2:36][CH:35]([NH:37][C:17](=[O:19])[C:16]3[CH:20]=[CH:21][CH:22]=[C:14]([S:13][C:11]4[NH:10][N:9]=[C:8]([NH:7][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=5)[CH:12]=4)[CH:15]=3)[CH2:34]2)(=[O:31])=[O:32])=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 66602158HCID 66602158, compoundHCID 178524400HCID 178524400, compound

Product 1

HCID 178522452HCID 178522452, compoundYield 36.9%

Procedure

3-(3-(Pyridine-2-ylamino)-1H-pyrazol-5-ylthio)benzoic acid (0.050 g, 0.160 mmol) and tert-butyl 1-(4-fluoro-phenylsulfonyl)azetidin-3-ylcarbamate (0.063 g, 0.19 mmol) were treated as described in Example 3, except that the mixture was purified on Prep HPLC (MeCN/H2O/0.1% TFA). This afforded the title material (0.031 g, 30%, trifluoroacetic acid salt) as a solid. 1H NMR 400 MHz DMSO-d6 δ (ppm): 3.72 (2H, dd, J=8.46, 6.44 Hz), 4.00 (2 H, t, J=8.08 Hz), 4.35-4.52 (1 H, m), 6.43 (1 H, s), 6.91-7.03 (1 H, m), 7.18 (1 H, d, J=8.08 Hz), 7.34-7.40 (1 H, m), 7.44 (1 H, t, J=7.71 Hz), 7.50-7.59 (2 H, m), 7.60-7.69 (2 H, m), 7.82-7.98 (3 H, m), 8.20 (1 H, d, J=4.55 Hz), 8.96 (1 H, d, J=6.06 Hz), 10.62 (1 H, br.s). HPLC ret. time (Condition B): 4.125 min.; 91%. LCMS (+ESI, M+H+) m/z 525. HRMS: calc. 525.1179, found 525.1191.

Workup

  1. customwas purified on Prep HPLC (MeCN/H2O/0.1% TFA)

Sources & evidence

ORD record
ord-bda95d093977436ca87c5beea2ed8d0e
Source dataset
uspto-grants-2010_12
Patent number
US07851500B2

Reaction notes

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