2-Chlorobenzenesulfonyl chloride → HCID 66891802, compound

HRID 1162049Notes

Reaction equation

HRID 1162049 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.[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33](Cl)(=[O:35])=[O:34]>>[ClH:26].[ClH:26].[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]([NH:25][C:18]1[CH:17]=[C:16]([CH2:15][N:11]2[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]2)[C:24]2[O:23][CH:22]=[CH:21][C:20]=2[CH:19]=1)(=[O:35])=[O:34]

Participants

3

Reactant 2

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 66893769HCID 66893769, compound

Product 1

HCID 66891802HCID 66891802, compoundYield 60.9%

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 Step 2) and 2-chlorobenzenesulfonyl chloride (21 μL, 0.16 mmol). The crude material was purified with preparative HPLC (System B; 10-40% MeCN). The title compound (16 mg, 33%) was obtained as a colorless solid. HPLC 95%, RT=1.31 min (System A; 10-97% MeCN over 3 min), 96%, RT=1.17 min (System B; 10-97% MeCN over 3 min). 1H NMR (400 MHz, methanol-d4) δ ppm 2.25-2.37 (m, 2H) 3.41-3.48 (m, 2H) 3.48-3.59 (m, J=4.52 Hz, 2H) 3.69-3.75 (m, J=3.51 Hz, 2H) 3.74-3.83 (m, 2H) 4.70 (s, 2H) 6.86 (d, J=2.26 Hz, 1H) 7.36-7.41 (m, 1H) 7.42 (d, J=2.01 Hz, 1H) 7.51-7.59 (m, 3H) 7.85 (d, J=2.01 Hz, 1H) 8.00-8.04 (m, J=7.91, 1.13 Hz, 1H). MS (ESI+) for C20H22ClN3O3S m/z 420 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-c6c5e79d2a644ee4ae100b97fb3e53d9
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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