Chlorosulfamic acid → HCID 59380384, compound

HRID 2353854Notes

Reaction equation

HRID 2353854 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:18]3[C:25]4[CH:26]=[CH:27][C:28]([CH2:30][CH2:31][OH:32])=[CH:29][C:24]=4[S:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.Cl[S:34]([NH2:37])(=[O:36])=[O:35]>CN(C)C(=O)C>[S:34](=[O:36])(=[O:35])([O:32][CH2:31][CH2:30][C:28]1[CH:27]=[CH:26][C:25]2[C:18]3[C:17]([NH:16][C:4]4[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]5[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=5)=[C:2]([Cl:1])[CH:3]=4)=[N:22][CH:21]=[N:20][C:19]=3[S:23][C:24]=2[CH:29]=1)[NH2:37]

Participants

4

Reactant 2

HCID 24499Chlorosulfamic acidHCID 59380379HCID 59380379, compound

Product 1

HCID 59380384HCID 59380384, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}[1]benzothieno[2,3-d]pyrimidin-7-yl)ethanol (35 mg, 0.08 mmol, 1 equiv) in N,N-Dimethylacetamide (2 mL) was added chlorosulfonamide (87 mg, 0.76 mmol, 10 equiv) under nitrogen. The reaction mixture was stirred at rt for 15 h. The solvent was concentrated in vacuo. The crude material was separated by pre-HPLC to give a white solid (18.6 mg, 43%) as product. 1H-NMR (DMSO-d6) δ 9.0 (broad s, 1H), 8.60 (d, J=4.6 Hz, 1H), 8.54 (s, 1H), 8.53 (d, J=8.5 Hz, 1H), 8.03 (s, 1H), 7.88 (t, 1H), 7.77 (d, J=2.2 Hz, 1H), 7.59 (d, J=7.8 Hz, 1H), 7.54 (m, 2H), 7.37 (t, 1H), 7.26 (d, J=8.7 Hz, 1H), 5.32 (s, 2H), 4.36 (t, 2H), 3.19 (t, 2H); LCMS RT=3.08 min, [M+H]+=542.10

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customThe crude material was separated by pre-HPLC

Sources & evidence

ORD record
ord-28ddc96a860045249f997add8e278369
Source dataset
uspto-grants-2010_07
Patent number
US07750017B2

Reaction notes

Loading…