2,5-Dimethoxytetrahydrofuran → HCID 11202178, compound

HRID 1294631Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:22])=[C:6]([NH:8][S:9]([C:12]2[C:17]3=[N:18][S:19][N:20]=[C:16]3[CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:7]=1.CO[CH:31]1[CH2:35][CH2:34][CH:33](OC)O1>C(O)(=O)C.C(Cl)Cl>[N:23]1([C:21]([C:5]2[CH:4]=[CH:3][C:2]([N:1]3[CH:31]=[CH:35][CH:34]=[CH:33]3)=[CH:7][C:6]=2[NH:8][S:9]([C:12]2[C:17]3=[N:18][S:19][N:20]=[C:16]3[CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[O:22])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirred solution of benzo[1,2,5]thiadiazole-4-sulfonic acid [5-amino-2-(piperidine-1-carbonyl)-phenyl]-amide (EXAMPLE 24; 25 mg, 0.06 mmol) in glacial acetic acid (3 mL) was added 2,5-dimethoxytetrahydrofuran (8 μL, 0.06 mmol). The reaction mixture was heated to 120° C. for 45 min after which it was cooled to room temperature. The mixture was taken up in 4 mL of DCM and washed with water. The organic layer was removed, dried, and purified by preparative reversed-phase HPLC to afford the title compound (12 mg, 0.02 mmol, 43%). MS (ESI): m/z 468 [M+H]+, 490 [M+Na]+. HPLC (reversed-phase): RT=9.71 mm (single peak). 1H NMR (400 MHz, CDCl3): (rotameric broadening) 9.15 (s, 1H), 8.26 (dd, J=7.0, 1.0 Hz, 1H), 8.22 (dd, J=8.8, 1.0 Hz, 1H), 7.74 (d, J=2.1 Hz, 1H), 7.67 (dd, J=8.8, 7 Hz, 1H), 7.10 (d, J=8.3 Hz, 1H), 7.05 (m, 3H), 6.35 (t, J=2.2 Hz, 2H), 3.23 (bs, 4H), 1.61 (m, 2H), 1.48 (bs, 4H).

Workup

temperaturewas cooled to room temperature
washwashed with water
customThe organic layer was removed
customdried
custompurified by preparative reversed-phase HPLC

Sources & evidence

ORD record: ord-4cfec1972c944f5f879c93b11cb1c6e2
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241759B2

Reaction notes

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