o-Toluenesulfonyl chloride → HCID 131728388, compound

HRID 1162050Notes

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.[CH3:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]([Cl:36])(=[O:35])=[O:34]>>[ClH:36].[ClH:36].[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:33]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[CH3:26])(=[O:35])=[O:34])[CH:17]=2)[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

Reactant 2

HCID 8623o-Toluenesulfonyl chloride

HCID 66893769HCID 66893769, compound

Product 1

HCID 131728388HCID 131728388, compoundYield 34.4%

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-methylbenzenesulfonyl chloride (23 μL, 0.16 mmol). The title compound (13 mg, 28%) was obtained as a colorless solid. HPLC 99%, RT=1.35 min (System A; 10-97% MeCN over 3 min), 100%, RT=1.22 min (System B; 10-97% MeCN over 3 min). 1H NMR (400 MHz, methanol-d4) δ ppm 2.26-2.32 (m, 2H) 2.66 (s, 3H) 3.40-3.60 (m, 4H) 3.69-3.83 (m, 4H) 4.69 (s, 2H) 6.86 (d, J=2.26 Hz, 1H) 7.23-7.29 (m, 1H) 7.32-7.38 (m, 2H) 7.41-7.46 (m, 1H) 7.47 (d, J=2.26 Hz, 1H) 7.84-7.90 (m, 2H). MS (ESI+) for C21H25N3O3S m/z 400 (M+H)+.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-f14222b49b1c42a4870bf9e75fa27a94
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820675B2

Reaction notes

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