o-Toluenesulfonyl chloride → HCID 131728386, compound

HRID 1162047Notes

Reaction equation

HRID 1162047 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.[CH3:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32]([Cl:35])(=[O:34])=[O:33]>>[ClH:35].[ClH:35].[CH3:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32]([NH:24][C:17]1[CH:16]=[C:15]([CH2:14][N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[C:23]2[O:22][CH:21]=[CH:20][C:19]=2[CH:18]=1)(=[O:34])=[O:33]

Participants

3

Reactant 2

HCID 8623o-Toluenesulfonyl chlorideHCID 668930201,1-Dimethylethyl 4-[(5-amino-7-benzofuranyl)methyl]-1-piperazinecarboxylate

Product 1

HCID 131728386HCID 131728386, compoundYield 24.2%

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-methylbenzenesulfonyl chloride (26 μL, 0.18 mmol). The crude product was purified with preparative HPLC (System B; 10-40% MeCN). The title compound (10 mg, 19%) was obtained as a colorless solid. HPLC 99%, RT=1.41 min (System A; 10-97% MeCN over 3 min), 99%, RT=1.26 min (System B; 10-97% MeCN over 3 min). 1H NMR (400 MHz, methanol-d4) δ ppm 2.66 (s, 3H) 3.50-3.65 (m, 8H) 4.67 (s, 2H) 6.86 (d, J=2.01 Hz, 1H) 7.22-7.29 (m, 1H) 7.30-7.37 (m, 2H) 7.40-7.48 (m, 2H) 7.81-7.90 (m, 2H). MS (ESI+) for C20H23N3O3S m/z 386 (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-09056654cd1b46f4aa12aae0d01318d9
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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