o-Toluenesulfonyl chloride → HCID 131728394, compound

HRID 1162063Notes

Reaction equation

HRID 1162063 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.[C:26]1([CH3:36])[C:27]([S:32]([Cl:35])(=[O:34])=[O:33])=[CH:28][CH:29]=[CH:30][CH:31]=1>>[ClH:35].[ClH:35].[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:32]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH3:36])(=[O:34])=[O:33])[CH:3]=1

Participants

3

Reactant 2

HCID 8623o-Toluenesulfonyl chlorideHCID 66892831HCID 66892831, compound

Product 1

HCID 131728394HCID 131728394, compoundYield 42.5%

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 o-toluenesulfonyl chloride (22 μL, 0.15 mmol). The title compound (15 mg, 31%) was obtained as an off-white solid. HPLC 98%, RT=1.37 min (System A; 10-97% MeCN over 3 min), 97%, RT=1.21 min (System B; 10-97% MeCN over 3 min). 1H NMR (400 MHz, methanol-d4) δ ppm 2.28-2.34 (m, 1H) 2.66 (s, 3H) 2.67-2.72 (m, 1H) 3.52-3.59 (m, J=13.68, 2.64 Hz, 1H) 3.63-3.76 (m, 1H) 3.85-3.93 (m, J=12.80 Hz, 1H) 4.45-4.51 (m, 1H) 4.65 (s, 1H) 4.69-4.78 (m, 1H) 4.78-4.83 (m, 2H) 6.86 (d, J=2.26 Hz, 1H) 7.23-7.29 (m, 1H) 7.31-7.36 (m, J=7.53 Hz, 1H) 7.37-7.46 (m, 2H) 7.48 (d, J=2.26 Hz, 1H) 7.84-7.88 (m, 2H). MS (ESI+) for C21H23N3O3S m/z 398 (M+H)+.

Sources & evidence

ORD record
ord-9a610964a5d4466ab8ae5b709b4bdb3d
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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