Ethanesulfonyl chloride → HCID 86615493, compound

HRID 2358658Notes

Reaction equation

HRID 2358658 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]([CH2:27][CH2:28][CH3:29])=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[CH:3]=1.[CH2:30]([S:32](Cl)(=[O:34])=[O:33])[CH3:31].C(N(CC)C(C)C)(C)C>CN(C1C=CN=CC=1)C.ClC(Cl)C>[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:32]([CH2:30][CH3:31])(=[O:34])=[O:33])=[CH:13][CH:14]=2)=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[N:22][C:23]([CH2:27][CH2:28][CH3:29])=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 11667Ethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 24897973HCID 24897973, compound

Product 1

HCID 86615493HCID 86615493, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

The product from Example 6 (100 mg, 0.228 mmol) was reacted with ethane sulfonyl chloride (28 mg, 0.228 mmol), N,N-diisopropylethylamine (88.5 mg, 0.685 mmol), and catalytic DMAP in dichloroethane for 18 h giving the crude title compound which was purified by HPLC with TFA providing the product as the trifluoroacetic acid (30 mg, 22%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.97 (t, J=7.35 Hz, 3 H) 1.34 (t, J=7.17 Hz, 3 H) 1.79-1.87 (m, 2 H) 2.40 (s, 3 H) 2.98 (t, J=7.54 Hz, 2 H) 3.47 (q, J=7.35 Hz, 2 H) 6.34 (d, J=7.35 Hz, 1 H) 7.14-7.19 (m, 2 H) 7.27 (d, 2 H) 7.39 (s, 2 H) 7.46 (d, 1 H) 7.78 (d, J=8.46 Hz, 1 H) 8.39 (d, J=6.99 Hz, 1 H) 8.92 (d, J=8.82 Hz, 1 H); MS (ESI+) m/z 494 (M+H)+.

Sources & evidence

ORD record
ord-e0c1518c63304f5ebdc47d8120a93240
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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