Lithium Hydroxide → HCID 71558548, compound

HRID 1022046Notes

Reaction equation

HRID 1022046 reaction equation
C([O:4][CH2:5][C:6]1[C:7]([N:36]2[CH2:48][CH2:47][N:39]3[C:40]4[CH2:41][CH2:42][CH2:43][CH2:44][C:45]=4[CH:46]=[C:38]3[C:37]2=[O:49])=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[C:16]([NH:18][C:19]2[N:20]=[CH:21][N:22]([CH:24]3[CH2:29][CH2:28][N:27]([CH:30]4[CH2:33][O:32][CH2:31]4)[CH2:26][CH2:25]3)[CH:23]=2)[C:15](=[O:34])[N:14]([CH3:35])[CH:13]=1)(=O)C.[OH-].[Li+]>C(O)(C)C.C1COCC1.O>[OH:4][CH2:5][C:6]1[C:7]([N:36]2[CH2:48][CH2:47][N:39]3[C:40]4[CH2:41][CH2:42][CH2:43][CH2:44][C:45]=4[CH:46]=[C:38]3[C:37]2=[O:49])=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[C:16]([NH:18][C:19]2[N:20]=[CH:21][N:22]([CH:24]3[CH2:29][CH2:28][N:27]([CH:30]4[CH2:33][O:32][CH2:31]4)[CH2:26][CH2:25]3)[CH:23]=2)[C:15](=[O:34])[N:14]([CH3:35])[CH:13]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86684461HCID 86684461, compound

Product 1

HCID 71558548HCID 71558548, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 22722550Tetrahydrofuran water isopropanolSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 243g (80 mg, 0.12 mmol) and lithium hydroxide (100 mg, 2.4 mmol) in i-propanol/THF/water (2:2:1, 8 mL) was stirred at 35° C. for 30 mins. The reaction mixture was then concentrated under reduced pressure. To the residue was added water and the resulting mixture was extracted with dichloromethane three times. The combined organic layer was concentrated under reduced pressure and the resulting residue was purified by reverse-phase prep-HPLC to afford 243 (28.0 mg, 30%). MS-ESI: [M+H]+ 625.4. 1H NMR (500 MHz, DMSO-d6) δ 8.48 (d, J=6.5 Hz, 1H), 7.54 (d, J=1.5 Hz, 1H), 7.53 (s, 1H), 7.45 (d, J=3.0 Hz, 1H), 7.35-7.34 (m, 2H), 7.11 (d, J=1.0 Hz, 1H), 6.58 (s, 1H), 5.14 (bs, 1H), 4.54 (t, J=7.5 Hz, 2H), 4.43-4.40 (m, 4H), 4.23-4.11 (m, 3H), 3.99-3.96 (m, 1H), 3.91-3.84 (m, 1H), 3.59 (s, 3H), 3.43-3.39 (m, 1H), 2.77-2.76 (m, 2H), 2.62-2.57 (m, 2H), 2.47-2.46 (m, 2H), 1.94-1.89 (m, 6H), 1.79-1.78 (m, 2H), 1.69-1.66 (m, 2H).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additionTo the residue was added water
  3. extractionthe resulting mixture was extracted with dichloromethane three times
  4. concentrationThe combined organic layer was concentrated under reduced pressure
  5. customthe resulting residue was purified by reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-3a8424273a18439682d651d649ca4d18
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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