Ethanesulfonyl chloride → HCID 86615487, compound

HRID 2358623Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[N:22][C:23]([CH3:27])=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[CH:3]=1.[CH2:28]([S:30](Cl)(=[O:32])=[O:31])[CH3:29]>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][S:30]([CH2:28][CH3:29])(=[O:32])=[O:31])=[CH:13][CH:14]=2)=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[N:22][C:23]([CH3:27])=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[CH:3]=1

Participants

Reactant 2

HCID 11667Ethanesulfonyl chloride

HCID 24897972HCID 24897972, compound

Product 1

HCID 86615487HCID 86615487, compound

Procedure

The product from Example 5 (100 mg, 0.24 mmol) was reacted with ethanesulfonyl chloride (31.0 mg, 0.24 mmol) for 18 h following the procedure from Example 58 giving the crude title compound which was purified by HPLC with TFA providing the trifluoroacetic acid salt (20 mg, 14%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 10.98 (s, 1H) 8.89 (d, J=8.46 Hz, 1H) 8.39 (d, J=6.99 Hz, 1H) 7.76 (d, J=8.82 Hz, 1H) 7.45-7.50 (m, 1H) 7.36-7.42 (m, 2H) 7.25 (d, 2H) 7.17 (d, 2H) 6.33 (d, J=6.99 Hz, 1H) 3.47 (q, J=7.35 Hz, 2H) 2.75 (s, 3H) 2.40 (s, 3H) 1.34 (t, J=7.35 Hz, 3H); MS (DCI NH3+) m/z 466 (M+H)+.

Sources & evidence

ORD record: ord-04465b8d0c284c3790e6ab2a9cf64479
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763731B2

Reaction notes

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