2-Thiophenesulfonyl chloride → HCID 131728387, compound

HRID 1162048Notes

Reaction equation

HRID 1162048 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[C:23]3[O:22][CH:21]=[CH:20][C:19]=3[CH:18]=[C:17]([NH2:24])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[S:30]([Cl:33])(=[O:32])=[O:31]>>[ClH:33].[ClH:33].[N:11]1([CH2:14][C:15]2[C:23]3[O:22][CH:21]=[CH:20][C:19]=3[CH:18]=[C:17]([NH:24][S:30]([C:26]3[S:25][CH:29]=[CH:28][CH:27]=3)(=[O:32])=[O:31])[CH:16]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 855182-Thiophenesulfonyl chloride2×HCID 668930201,1-Dimethylethyl 4-[(5-amino-7-benzofuranyl)methyl]-1-piperazinecarboxylate

Product 1

HCID 131728387HCID 131728387, compoundYield 7.4%

Procedure

The title compound was prepared according to the procedure of Example 106, Step 3, starting from 4-(5-amino-benzofuran-7-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester (40 mg, 0.12 mmol; obtained in Example 106, Step 2) and 2-thiophenesulfonyl chloride (33 mg, 0.18 mmol). Additional 2-thiophenesulfonyl chloride (10 mg, 0.05 mmol) was added with continued stirring for 1 h. The crude product was purified with preparative HPLC (System B; 10-40% MeCN). The title compound (3 mg, 6%) was obtained as a colorless solid. HPLC 95%, RT=1.25 min (System A; 10-97% MeCN over 3 min), 95%, RT=1.11 min (System B; 10-97% MeCN over 3 min). 1H NMR (400 MHz, methanol-d4) δ ppm 3.43-3.49 (m, 4H) 3.50-3.57 (m, 4H) 4.59 (s, 2H) 6.90 (d, J=2.26 Hz, 1H) 7.05 (dd, J=5.02, 3.76 Hz, 1H) 7.35 (d, J=2.26 Hz, 1H) 7.45-7.50 (m, 2H) 7.70 (dd, J=5.02, 1.51 Hz, 1H) 7.88 (d, J=2.26 Hz, 1H). MS (ESI+) for C17H19N3O3S2 m/z 378 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified with preparative HPLC (System B; 10-40% MeCN)

Sources & evidence

ORD record
ord-6db5a8785f494b4bb2dcd1f7ef7439a0
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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