2-Trifluoromethylbenzenesulphonyl chloride → HCID 131728393, compound

HRID 1162062Notes

Reaction equation

HRID 1162062 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:11][N:12]2[CH2:17][C@@H:16]3[CH2:18][C@H:13]2[CH2:14][N:15]3C(OC(C)(C)C)=O)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[F:26][C:27]([F:39])([F:38])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34]([Cl:37])(=[O:36])=[O:35]>>[ClH:37].[ClH:37].[C@H:13]12[CH2:18][C@H:16]([NH:15][CH2:14]1)[CH2:17][N:12]2[CH2:11][C:4]1[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=[C:2]([NH:1][S:34]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[C:27]([F:26])([F:38])[F:39])(=[O:36])=[O:35])[CH:3]=1

Participants

3

Reactant 2

HCID 1366162-Trifluoromethylbenzenesulphonyl chlorideHCID 66892831HCID 66892831, compound

Product 1

HCID 131728393HCID 131728393, compoundYield 45.8%

Procedure

starting from tert-butyl (1S,4S)-5-[(5-amino-1-benzofuran-7-yl)methyl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (44 mg crude starting material, 0.10 mmol; obtained in Example 118, Step 2) and 2-(trifluoromethyl)benzenesulfonyl chloride (24 μL, 0.15 mmol). The title compound (18 mg, 34%) was obtained as an off-white solid. HPLC 99%, RT=1.46 min (System A; 10-97% MeCN over 3 min), 100%, RT=1.29 min (System B; 10-97% MeCN over 3 min). 1H NMR (400 MHz, methanol-d4) δ ppm 2.31-2.37 (m, J=13.05 Hz, 1H) 2.65-2.78 (m, J=6.27 Hz, 1H) 3.53-3.60 (m, J=13.43, 2.89 Hz, 1H) 3.67-3.76 (m, 1H) 3.88-3.96 (m, J=12.80 Hz, 1H) 4.51 (s, 1H) 4.66 (s, 1H) 4.72-4.79 (m, 1H) 4.84 (d, 2H) 6.88 (d, J=2.01 Hz, 1H) 7.46 (d, J=2.01 Hz, 1H) 7.51 (d, J=2.01 Hz, 1H) 7.68-7.75 (m, 2H) 7.88 (d, J=2.26 Hz, 1H) 7.89-7.94 (m, 1H) 8.09-8.13 (m, 1H). MS (ESI+) for C21H20F3N3O3S m/z 452 (M+H)+.

Sources & evidence

ORD record
ord-d73b14eececd4e82b92b26cb9b3b7519
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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