Lithium Hydroxide → HCID 67441998, compound

HRID 1253581Notes

Reaction equation

HRID 1253581 reaction equation
C([O:4][CH2:5][C:6]([N:8]([CH2:13][C:14]1[N:18]([CH3:19])[C:17]([C:20]2[S:28][C:27]3[C:22](=[N:23][CH:24]=[CH:25][C:26]=3[O:29][C:30]3[CH:35]=[CH:34][C:33]([NH:36][C:37]([NH:39][CH:40]4[CH2:42][CH2:41]4)=[O:38])=[CH:32][C:31]=3[F:43])[CH:21]=2)=[N:16][CH:15]=1)[CH2:9][CH2:10][O:11][CH3:12])=[O:7])(=O)C.[Li+].[OH-]>C1COCC1.O>[CH:40]1([NH:39][C:37](=[O:38])[NH:36][C:33]2[CH:34]=[CH:35][C:30]([O:29][C:26]3[CH:25]=[CH:24][N:23]=[C:22]4[CH:21]=[C:20]([C:17]5[N:18]([CH3:19])[C:14]([CH2:13][N:8]([CH2:9][CH2:10][O:11][CH3:12])[C:6](=[O:7])[CH2:5][OH:4])=[CH:15][N:16]=5)[S:28][C:27]=34)=[C:31]([F:43])[CH:32]=2)[CH2:41][CH2:42]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67440451HCID 67440451, compound

Product 1

HCID 67441998HCID 67441998, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 208 (104 mg, 0.170 mmol) in THF (18 mL) was added a solution of LiOH (32.6 mg, 1.362 mmol) in water (6 mL) and the mixture was stirred for 2 hr at room temperature before concentration. The residue was purified by Biotage (MeOH/DCM, 0-20%, SNAP 25 g cartridge) to give title compound 209 (40 mg, 0.070 mmol, 41% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.75 (s, 1H), 8.55 (d, 1H, J=5.3 Hz), 7.94 (s, 1H), 7.75 (dd, 1H, J1=2.3 Hz, J2=13.5 Hz), 7.41 (t, 1H, J=9.0 Hz), 7.24-7.22 (m, 1H), 7.09 (s, 1H), 6.70 (d, 1H, J=5.5 Hz), 6.60 (m, 1H), 4.74 (s, 2H), 4.68-4.66 (m, 1H), 4.24 (d, J=5.7 Hz), 3.87 (s, 3H), 3.45 (m, 2H), 3.35 (s, 3H), 3.28 (m, 2H), 2.60-2.57 (m, 1H), 0.71-0.67 (m, 2H), 0.48-0.45 (m, 2H). MS: 569.6 (MH)+

Workup

  1. customThe residue was purified by Biotage (MeOH/DCM, 0-20%, SNAP 25 g cartridge)

Sources & evidence

ORD record
ord-7dd200de9e12403c95aa936171a20d28
Source dataset
uspto-grants-2013_06
Patent number
US08455484B2

Reaction notes

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