Tert-butyl 1-(phenylsulfonyl)azetidin-3-ylcarbamate → HCID 178522451, compound

HRID 2262814Notes

Reaction equation

HRID 2262814 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.[C:23]1([S:29]([N:32]2[CH2:35][CH:34]([NH:36]C(=O)OC(C)(C)C)[CH2:33]2)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:23]1([S:29]([N:32]2[CH2:33][CH:34]([NH:36][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)[CH2:35]2)(=[O:30])=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 66602360Tert-butyl 1-(phenylsulfonyl)azetidin-3-ylcarbamateHCID 178524400HCID 178524400, compound

Product 1

HCID 178522451HCID 178522451, compoundYield 50.4%

Procedure

3-(3-(Pyridine-2-ylamino)-1H-pyrazol-5-ylthio)benzoic acid (0.060 g, 0.192 mmol) and tert-butyl 1-(phenylsulfonyl)azetidin-3-ylcarbamate (0.060 g, 0.192 mmol) were treated as described in Example 3, except that the purification was done on Prep HPLC (MeCN/H2O/0.1% TFA). This afforded the title material (0.049 g, 41%, trifluoroacetic acid salt) as a solid. 1H NMR 400 MHz DMSO-d6 δ (ppm): 3.73 (2H, dd, J=8.72, 6.44 Hz), 3.99 (2H, t, J=8.21 Hz), 4.32-4.46 (1H, m), 6.43 (1H, s), 6.99 (1H, t, J=6.19 Hz), 7.20 (1H, d, J=8.59 Hz), 7.32-7.50 (2H, m), 7.59-7.74 (4H, m), 7.75-7.82 (1H, m), 7.82-7.95 (3H, m), 8.21 (1H, d, J=4.55 Hz), 8.98 (1H, d, J=6.06 Hz), 10.76 (1H, s). HPLC ret. time (Condition B): 3.950 min.; 85%. LCMS (+ESI, M+H+) m/z 507, (−ESI M−H+) m/z 505, HRMS: calc. 507.1273, found 507.1264.

Workup

  1. customas described in Example 3, except that the purification

Sources & evidence

ORD record
ord-80a4fef8eaf04d6ab9aa514010842f93
Source dataset
uspto-grants-2010_12
Patent number
US07851500B2

Reaction notes

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