2-Thiophenesulfonyl chloride → HCID 66893886, compound

HRID 1162051Notes

Reaction equation

HRID 1162051 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][C:16]2[C:24]3[O:23][CH:22]=[CH:21][C:20]=3[CH:19]=[C:18]([NH2:25])[CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[S:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[S:31]([Cl:34])(=[O:33])=[O:32]>>[ClH:34].[ClH:34].[N:11]1([CH2:15][C:16]2[C:24]3[O:23][CH:22]=[CH:21][C:20]=3[CH:19]=[C:18]([NH:25][S:31]([C:27]3[S:26][CH:30]=[CH:29][CH:28]=3)(=[O:33])=[O:32])[CH:17]=2)[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

3

Reactant 2

HCID 855182-Thiophenesulfonyl chloride2×HCID 66893769HCID 66893769, compound

Product 1

HCID 66893886HCID 66893886, compoundYield 26.9%

Procedure

The title compound was prepared according to the procedure of Example 106, Step 3, starting from 4-(5-amino-benzofuran-7-ylmethyl)-1,4-diazepane-1-carboxylic acid tert-butyl ester (36 mg, 0.10 mmol; obtained in Example 109, Step 2) and 2-thiophenesulfonyl chloride (29 mg, 0.16 mmol). Additional 2-thiophenesulfonyl chloride (10 mg, 0.06 mmol) was added with continuous stirring for 1 h. The title compound (10 mg, 22%) was obtained as a colorless solid. HPLC 100%, RT=1.20 min (System A; 10-97% MeCN over 3 min), 100%, RT=1.06 min (System B; 10-97% MeCN over 3 min). 1H NMR (400 MHz, methanol-d4) δ ppm 2.20-2.29 (m, 2H) 3.34-3.41 (m, 2H) 3.41-3.55 (m, 2H) 3.63-3.69 (m, 2H) 3.69-3.77 (m, 2H) 4.66 (s, 2H) 6.84 (d, J=2.26 Hz, 1H) 6.98 (dd, J=5.02, 3.76 Hz, 1H) 7.32 (d, J=2.01 Hz, 1H) 7.42 (dd, J=3.76, 1.25 Hz, 1H) 7.47 (d, J=2.26 Hz, 1H) 7.63 (dd, J=5.02, 1.25 Hz, 1H) 7.82 (d, J=2.26 Hz, 1H). MS (ESI+) for C18H21N3O3S2 m/z 392 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-d4a52f6818eb4a2d936b3d01c285c9d8
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

Loading…