Sodium Hydroxide → HCID 87191648, compound

HRID 2089056Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH:11]([NH:15][S:16]([CH:19]3[CH2:21][CH2:20]3)(=[O:18])=[O:17])[CH2:10]2)[CH:5]=[C:4]([C:22]2[C:30]3[C:25](=[N:26][CH:27]=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24](S(C3C=CC=CC=3)(=O)=O)[CH:23]=2)[CH:3]=1.[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH:11]([NH:15][S:16]([CH:19]3[CH2:20][CH2:21]3)(=[O:18])=[O:17])[CH2:10]2)[CH:5]=[C:4]([C:22]2[C:30]3[C:25](=[N:26][CH:27]=[C:28]([O:31][CH3:32])[CH:29]=3)[NH:24][CH:23]=2)[CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of Example 260c (0.083 g, 0.135 mmol) in dioxane (2 mL) was treated with 20% NaOH (0.08 mL, 0.135 mmol). The mixture was heated at 70° C. for 90 minutes. The solvent was evaporated. The residue was treated with water and sonicated. The solid was filtered, washed with water, and purified by reverse-phase HPLC as described in Example 56 to give the title compound (43.2 mg) as trifluoroacetic acid salts. 1H NMR (400 MHz, DMSO-d6) ppm 0.83-0.98 (m, 4H), 0.98-1.26 (m, 3H), 1.38 (m, 1H), 1.74 (m, 1H), 1.86-1.98 (m, 2H), 2.31 (d, J=13.43 Hz, 1H), 2.56 (m, 1H), 3.24 (m, 1H, 3.73 (m, 1H), 3.90 (s, 3H), 6.81 (s, 1H), 6.88 (d, J=1.22 Hz, 1H), 7.14 (d, J=8.24 Hz, 1H), 7.79 (d, J=2.75 Hz, 1H), 8.09 (dd, J=7.93, 2.75 Hz, 2H), 12.04 (s, 1H). MS (ESI+) m/z 476.2 (M+H)+.

Workup

customThe solvent was evaporated
additionThe residue was treated with water
customsonicated
filtrationThe solid was filtered
washwashed with water
custompurified by reverse-phase HPLC

Sources & evidence

ORD record: ord-67455fee1bf14a6898e83ae58978c8c6
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08435980B2

Reaction notes

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