Sodium Hydroxide → HCID 118235787, compound

HRID 626988Notes

Reaction equation

[OH-].[Na+:2].[F:3][CH:4]([F:43])[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]1[N:17]2[CH:18]=[C:19]([C:23]3[CH:24]=[N:25][C:26]([N:29]4[CH2:34][CH2:33][C:32]([CH2:40][OH:41])([C:35]([O:37]CC)=[O:36])[CH2:31][CH2:30]4)=[N:27][CH:28]=3)[C:20]([F:22])=[CH:21][C:16]2=[N:15][C:14]=1[CH3:42]>C1COCC1.CO.O>[F:43][CH:4]([F:3])[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]1[N:17]2[CH:18]=[C:19]([C:23]3[CH:24]=[N:25][C:26]([N:29]4[CH2:30][CH2:31][C:32]([CH2:40][OH:41])([C:35]([O-:37])=[O:36])[CH2:33][CH2:34]4)=[N:27][CH:28]=3)[C:20]([F:22])=[CH:21][C:16]2=[N:15][C:14]=1[CH3:42].[Na+:2]

Participants

Conditions

Temperature: 70 °C

Procedure

Sodium hydroxide (7 mg, 0.175 mmol) was added to a solution of Example 174 (0.1 g, 0.176 mmol) in THF-MeOH-water, 1:1:1 (4 mL). The mixture was stirred at 70° C. for 2 h. The mixture was concentrated and diluted with water, then washed with EtOAc. The aqueous layer was freeze-dried. The resulting material (95 mg) was purified by HPLC to give the title compound (30 mg, 30%) as a white lyophilised solid. δH (400 MHz, DMSO-d6) 8.48 (m, 2H), 8.34 (d, J 7.5 Hz, 1H), 7.46 (m, 1H), 7.30 (m, 1H), 7.26 (t, J 72 Hz, 1H), 7.19 (m, 1H), 7.14 (td, J 7.5, 1.1 Hz, 1H), 7.02 (m, 1H), 4.39 (m, 2H), 4.34 (s, 2H), 3.43 (s, 2H), 3.23 (m, 2H), 2.28 (s, 3H), 1.98 (m, 2H), 1.40 (m, 2H). LCMS (pH 10): MH+ 542, RT 1.44 minutes.

Workup

concentrationThe mixture was concentrated
additiondiluted with water
washwashed with EtOAc
customThe aqueous layer was freeze-dried
customThe resulting material (95 mg) was purified by HPLC

Sources & evidence

ORD record: ord-73ef7ead0b324253b51ccd62d0c17b36
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309243B2

Reaction notes

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