Chlorosulfamic acid → HCID 68493881, compound

HRID 1944208Notes

Reaction equation

HRID 1944208 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][C:8]([CH3:23])([CH3:22])[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[CH2:10]2)=[CH:5][C:4]=1[O:24][Si](C(C)C)(C(C)C)C(C)C.[NH2:35][S:36](Cl)(=[O:38])=[O:37]>CC(N(C)C)=O>[S:36](=[O:38])(=[O:37])([O:24][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[CH2:10][N:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)[C:8]([CH3:23])([CH3:22])[CH2:7]2)[NH2:35]

Participants

4

Reactant 2

HCID 24499Chlorosulfamic acidHCID 68497112HCID 68497112, compound

Product 1

HCID 68493881HCID 68493881, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Sulfamoylation of 226 with H2NSO2Cl and DMA as described above afforded the title compound (86 mg, 89%) as a colourless foam. 1H NMR (400 MHz; DMSO-d6) 1.14 (6H, s, 2×CH3), 2.69 (2H, s, CH2), 3.43 (2H, s, CH2), 3.62 (2H, s, CH2), 3.73 (3H, s, OCH3), 3.75 (3H, s, OCH3), 6.80 (1H, dd, J=8.0, 2.0 Hz, CH), 6.83 (1H, s, CH), 6.89-6.94 (3H, m, 3×CH), 7.23 (1H, t, J=8.0 Hz, CH), 7.79 (2H, s, NH2). 13C NMR (100 MHz; DMSO-d6) 42.80 (CH2), 49.42 (CH2), 52.05 (C), 53.0 (CH2), 54.94 (OCH3), 55.79 (OCH3), 111.83 (CH), 112.97 (CH), 114.10 (CH), 120.30 (CH), 120.61 (CH), 125.77 (C), 129.25 (CH), 133.04 (C), 136.80 (C), 142.19 (C), 149.88 (C), 159.28 (C). LC/MS (ES+) tr=1.14 min, m/z 407.28 (M++H). HRMS (ES+) cald. for C20H27N2O5S (M++H) 407.1635, found 407.1636. HPLC tr=2.10 min (>98%).

Sources & evidence

ORD record
ord-9ed37fe0ad5647469f1b3f0d73fc79f9
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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