Chlorosulfamic acid → 1-((2-Cyano-3-(sulfamoylamino)phenoxy)methyl)-N-propylcyclopropanecarboxamide

HRID 711798Notes

Reaction equation

HRID 711798 reaction equation
[NH2:1][C:2]1[C:3]([C:19]#[N:20])=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][CH2:6][C:7]1([C:10]([NH:12][CH2:13][CH2:14][CH3:15])=[O:11])[CH2:9][CH2:8]1.[S:21](Cl)(=[O:24])(=[O:23])[NH2:22]>>[C:19]([C:3]1[C:2]([NH:1][S:21](=[O:24])(=[O:23])[NH2:22])=[CH:18][CH:17]=[CH:16][C:4]=1[O:5][CH2:6][C:7]1([C:10]([NH:12][CH2:13][CH2:14][CH3:15])=[O:11])[CH2:8][CH2:9]1)#[N:20]

Participants

3

Reactant 2

HCID 24499Chlorosulfamic acidHCID 667463181-((3-amino-2-cyanophenoxy)methyl)-N-propylcyclopropanecarboxamide

Product 1

HCID 667459991-((2-Cyano-3-(sulfamoylamino)phenoxy)methyl)-N-propylcyclopropanecarboxamideYield 78%

Procedure

Prepared as in Example 111a from 1-((3-amino-2-cyanophenoxy)methyl)-N-propylcyclopropanecarboxamide (Example 198b) and sulfamoyl chloride in 78% yield as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ 9.45 (broad s, 1H), 7.51-7.61 (m, 2H), 7.26 (broad s, 2H), 7.16 (d, J=8.0 Hz, 1H), 6.91 (d, J=8.4 Hz, 1H), 4.24 (s, 2H), 3.04 (q, J=6.4 Hz, 2H), 1.43 (hex, J=7.6 Hz, 2H), 1.08-1.14 (m, 2H), 0.83-0.88 (m, 2H), 0.82 (t, J=7.2 Hz, 3H).

Sources & evidence

ORD record
ord-53964d7d0df04e3bbd70da443041b902
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

Loading…