Chlorosulfamic acid → tert-butyl 6-(4-amino-2,2-dioxo-1H-benzo[c][1,2,6]thiadiazin-5-yloxy)hexylcarbamate

HRID 711924Notes

Reaction equation

HRID 711924 reaction equation
[NH2:1][C:2]1[C:3]([C:23]#[N:24])=[C:4]([CH:20]=[CH:21][CH:22]=1)[O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].[S:25](Cl)(=[O:28])(=[O:27])[NH2:26]>>[NH2:24][C:23]1[C:3]2[C:4]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:20][CH:21]=[CH:22][C:2]=2[NH:1][S:25](=[O:28])(=[O:27])[N:26]=1

Participants

3

Reactant 2

HCID 24499Chlorosulfamic acidHCID 66746101Tert-butyl 6-(3-amino-2-cyanophenoxy)hexylcarbamate

Product 1

HCID 66746882tert-butyl 6-(4-amino-2,2-dioxo-1H-benzo[c][1,2,6]thiadiazin-5-yloxy)hexylcarbamateYield 59.5%

Procedure

Prepared as in Example 274 from tert-butyl 6-(3-amino-2-cyanophenoxy)hexylcarbamate (Example 281a) and sulfamoyl chloride in 59.5% yield. 1H NMR (400 MHz, DMSO-d6) δ 1.274 (m, 2H), 1.339 (s, 9H), 1.361 (m, 4H), 1.779 (pentet, J=7 Hz, 2H), 2.878 (q, J=6 Hz, 2H), 4.122 (t, J=6 Hz, 2H), 6.580 (d, J=8 Hz, 1H), 6.722 (d, J=8 Hz, 1H), 6.75 (br t, J=6 Hz, 1H), 7.428 (t, J=8 Hz, 1H), 7.798 (br. s, 1H), 8.323 (br. s, 1H), 10.921 (s, 1H). MS 413 (MH+).

Sources & evidence

ORD record
ord-d866a4e8eb9e445fa0f91dc0952f1013
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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