Water → HCID 90413177, compound

HRID 1522037Notes

Reaction equation

HRID 1522037 reaction equation
[F:1][C:2]1[C:3]([C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[O:35][CH3:36])=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:16][CH2:15][N:14]([CH:17]4[CH2:22][CH2:21][CH:20]([CH2:23][C:24]([O:26]C)=[O:25])[CH2:19][CH2:18]4)[CH2:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[OH-].[Li+].O>O1CCCC1.CO>[F:1][C:2]1[C:3]([C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[O:35][CH3:36])=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:16][CH2:15][N:14]([CH:17]4[CH2:22][CH2:21][CH:20]([CH2:23][C:24]([OH:26])=[O:25])[CH2:19][CH2:18]4)[CH2:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 90412102HCID 90412102, compound

Product 1

HCID 90413177HCID 90413177, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 298A (0.115 g, 0.232 mmol) and lithium hydroxide (0.011 g, 0.464 mmol) in tetrahydrofuran (3 mL), methanol (1.2 mL), and water (0.9 mL) was stirred overnight and concentrated. The residue was dissolved in 4 mL water and treated with 2M aqueous hydrogen chloride. The suspension was diluted with water, stirred for 15 minutes, filtered, washed with water, and vacuum oven-dried to give the title compound as a hydrochloride salt. 1H NMR (400 MHz, Methanol-d4) δ 1.13-1.28 (m, 1H), 1.55-1.95 (m, 4H), 1.95-2.07 (m, 2H), 2.17-2.27 (m, 3H), 2.43 (d, J=7.6 Hz, 1H), 2.87-2.95 (m, 2H), 3.30-3.38 (m, 2H), 3.77 (s, 4H), 4.00-4.08 (m, 2H), 6.33 (s, 1H), 6.41 (bs, 1H), 7.08-7.26 (m, 3H), 8.15 (d, J=2.8 Hz, 1H). MS (ESI+) m/z 482.0 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in 4 mL water
  3. additiontreated with 2M aqueous hydrogen chloride
  4. additionThe suspension was diluted with water
  5. filtrationfiltered
  6. washwashed with water, and vacuum
  7. customoven-dried

Sources & evidence

ORD record
ord-512e15e1b6a7481d89331bca52474746
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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