2-Chlorobenzenesulfonyl chloride → HCID 66894092, compound

HRID 1161993Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[O:19])[CH2:13][CH2:12]2)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[Cl:25]C1C=CC=CC=1S(Cl)(=O)=O.[Cl:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[S:43](NC1C=C(N2CCN(C(OC(C)(C)C)=O)CC2)C2OC=CC=2C=1)(=[O:45])=[O:44]>>[ClH:25].[Cl:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[S:43]([NH:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[O:19])[CH2:13][CH2:12]2)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1)(=[O:45])=[O:44]

Participants

Reactant 3

HCID 761872-Chlorobenzenesulfonyl chloride

HCID 66894206HCID 66894206, compound2×

HCID 69630494HCID 69630494, compound

Product 1

HCID 66894092HCID 66894092, compound

Procedure

2-[4-(5-Amino-1-benzofuran-7-yl)piperazin-1-yl]-N,N-diethylacetamide (0.095 g, 0.29 mmol; Intermediate 23) was reacted with 2-chlorobenzenesulfonyl chloride according to the procedure of Intermediate 19. Yield: 0.06 g (41%) after purification by preparative HPLC (System E; 20-50% MeCN). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08 (t, J=6.9 Hz, 3H) 1.15 (t, J=6.9 Hz, 3H) 3.09-3.43 (m, 7H) 3.55-3.65 (m, 2H) 3.67-3.76 (m, 2H) 4.39 (s, 2H) 6.62 (d, J=1.0 Hz, 1H) 6.86 (d, J=1.3 Hz, 1H) 6.93 (d, J=1.5 Hz, 1H) 7.47 (t, J=7.0 Hz, 1H) 7.60 (q, J=7.7 Hz, 2H) 7.91 (d, J=1.3 Hz, 1H) 8.01 (d, J=7.8 Hz, 1H) 10.08 (s, 1H) 10.46 (s, 1H). HPLC purity 92%, RT=1.85 min (System A; 10-97% MeCN over 3 min). MS (ESI+) m/z 505.2 (M+H)+.

Workup

customYield: 0.06 g (41%) after purification by preparative HPLC (System E; 20-50% MeCN)

Sources & evidence

ORD record: ord-8e3b5dd2010f4f01a9e2a6e053f214d7
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820675B2

Reaction notes

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