Diisopropylethylamine → HCID 86615499, compound

HRID 2358737Notes

Reaction equation

HRID 2358737 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=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.[CH:28]([S:31](Cl)(=[O:33])=[O:32])([CH3:30])[CH3:29].C(N(CC)C(C)C)(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([O:13][S:31]([CH:28]([CH3:30])[CH3:29])(=[O:33])=[O:32])=[CH:11][CH:12]=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

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 824082-Propanesulfonyl chlorideHCID 68456169HCID 68456169, compound

Product 1

HCID 86615499HCID 86615499, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The product from Example 165d (43 mg, 0.085 mmol) was reacted with isopropylsulfonyl chloride (14.5 mg, 0.102 mmol), N,N-diisopropylethylamine (33 mg, 0.255 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 (16 mg, 31%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.38 (d, J=6.99 Hz, 6 H) 2.73 (s, 3 H) 3.54-3.65 (m, 1 H) 6.69 (d, J=6.99 Hz, 1 H) 7.01 (d, J=9.19 Hz, 2 H) 7.20 (d, J=9.19 Hz, 2 H) 7.27 (d, J=8.82 Hz, 1 H) 7.60 (dd, J=8.82, 2.57 Hz, 1 H) 7.70-7.75 (m, 2 H) 8.51 (d, J=6.99 Hz, 1 H) 8.81 (d, J=8.82 Hz, 1 H); MS (ESI+) m/z 484 (M+H)+.

Sources & evidence

ORD record
ord-96e3e98a5e6541c0bea2543010074cb7
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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