Sodium Hydroxide → HCID 118235510, compound

HRID 626989Notes

Reaction equation

[OH-].[Na+:2].[F:3][CH:4]([F:42])[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[CH2:35][CH2:34][CH:33]5[C:31]([C:36]([O:38]CC)=[O:37])([CH2:32]5)[CH2:30]4)=[N:27][CH:28]=3)[C:20]([F:22])=[CH:21][C:16]2=[N:15][C:14]=1[CH3:41]>C1COCC1.CO.O>[F:42][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[CH2:35][CH2:34][CH:33]5[C:31]([C:36]([O-:38])=[O:37])([CH2:32]5)[CH2:30]4)=[N:27][CH:28]=3)[C:20]([F:22])=[CH:21][C:16]2=[N:15][C:14]=1[CH3:41].[Na+:2]

Participants

Conditions

Temperature: 70 °C

Procedure

Sodium hydroxide (7.5 mg, 0.188 mmol) was added to a solution of Example 177 (0.104 g, 0.188 mmol) in THF-MeOH-water, 1:1:1 (4 mL). The mixture was stirred at 70° C. for 3 h. The reaction mixture was concentrated, diluted with water and washed with diethyl ether, then the aqueous layer was freeze-dried, to give the title compound (100 mg, 100%) as a white lyophilised solid. δH (400 MHz, DMSO-d6) 8.21 (d, J 1.3 Hz, 2H), 8.12 (d, J 7.5 Hz, 1H), 7.22 (m, 1H), 7.08 (m, 1H), 7.05 (t, J 72, 76 Hz, 1H), 6.97 (m, 1H), 6.92 (m, 1H), 6.81 (dd, J 7.5, 1.1 Hz, 1H), 4.12 (s, 2H), 4.04 (m, 1H), 3.96 (m, 1H), 3.43 (m, 1H), 3.07 (m, 1H), 2.07 (s, 3H), 1.76 (m, 1H), 1.50 (m, 1H), 1.15 (m, 1H), 0.72 (dd, J 8.7, 2.9 Hz, 1H), 0.00 (dd, J 5.4, 3.2 Hz, 1H). LCMS (pH 10): MH+ 524, RT 1.56 minutes.

Workup

concentrationThe reaction mixture was concentrated
additiondiluted with water
washwashed with diethyl ether
customthe aqueous layer was freeze-dried

Sources & evidence

ORD record: ord-b2f76f7f18374cd3b827daac389aa24d
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309243B2

Reaction notes

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