Diisopropylethylamine → HCID 86615491, compound

HRID 2358656Notes

Reaction equation

HRID 2358656 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.[CH:30]([S:33](Cl)(=[O:35])=[O:34])([CH3:32])[CH3:31].C(N(CC)C(C)C)(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[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:33]([CH:30]([CH3:32])[CH3:31])(=[O:35])=[O:34])=[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 81531DiisopropylethylamineHCID 824082-Propanesulfonyl chlorideHCID 24897973HCID 24897973, compound

Product 1

HCID 86615491HCID 86615491, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The product from Example 6 (120 mg, 0.274 mmol) was reacted with isopropyl sulfonyl chloride (43 mg, 0.30 mmol), N,N-diisopropylethylamine (43 mg, 0.33 mmol), and catalytic DMAP in CH2Cl2 for 18 h giving the crude title compound which was purified by HPLC with TFA providing the product as the trifluoroacetic acid (40 mg, 23%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 8.75 (d, J=8.54 Hz, 1 H) 8.20 (d, J=6.71 Hz, 1 H) 7.58 (d, J=8.54 Hz, 1 H) 7.26 (d, J=7.93 Hz, 1 H) 7.17-7.21 (m, 2 H) 7.08 (d, J=9.16 Hz, 2 H) 6.95 (d, J=8.54 Hz, 2 H) 6.15 (d, J=6.71 Hz, 1 H) 3.43-3.51 (m, J=13.43, 1H) 2.79 (t, J=7.63, 7.63 Hz, 2 H) 2.20 (s, 3 H) 1.61-1.67 (m, 2 H) 1.21 (d, J=6.71 Hz, 6 H) 0.78 (t, J=7.32 Hz, 3 H); MS (ESI+) m/z 508 (M+H)+.

Sources & evidence

ORD record
ord-921d2164c1c346a7bd629f326fdaae35
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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