Sodium Hydroxide → HCID 67440527, compound

HRID 1400943Notes

Reaction equation

HRID 1400943 reaction equation
[CH:1]1([NH:4][C:5](=[O:47])[NH:6][C:7]2[CH:45]=[CH:44][C:10]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[N:26]=[CH:25][C:24]([CH2:27][N:28]([CH:35]6[CH2:38][N:37]([C:39](=[O:43])[NH:40][CH2:41][CH3:42])[CH2:36]6)[CH2:29][C:30]([O:32]CC)=[O:31])=[CH:23][CH:22]=5)[S:20][C:13]=34)=[C:9]([F:46])[CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([NH:4][C:5](=[O:47])[NH:6][C:7]2[CH:45]=[CH:44][C:10]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[N:26]=[CH:25][C:24]([CH2:27][N:28]([CH:35]6[CH2:36][N:37]([C:39](=[O:43])[NH:40][CH2:41][CH3:42])[CH2:38]6)[CH2:29][C:30]([OH:32])=[O:31])=[CH:23][CH:22]=5)[S:20][C:13]=34)=[C:9]([F:46])[CH:8]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67441845HCID 67441845, compound

Product 1

HCID 67440527HCID 67440527, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 433 (78 mg, 0.118 mmol) in MeOH (3 mL) was added 1N NaOH (0.59 mL, 0.59 mmol) and stirred at RT for 3 h. The mixture was then concentrated, diluted with water and the pH was adjusted to 6-7 by addition of 1N HCl. To the resulting suspension was added MeOH to dissolve the mixture clearly, and purified via Biotage [KP-C18-HS 30 g, gradient 20-95% (methanol/water)]. Title compound 434 was obtained as a white solid (79.5 mg, 60% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.94 (brs, 1H), 8.71 (s, 1H), 8.62-8.57 (m, 1H), 8.38 (d, J=5.6 Hz, 1H), 8.19 (s, 1H), 8.15 (d, J=8.0 Hz, 1H), 7.89 (dd, J=8.0, 2.0 Hz, 1H), 7.82 (dd, J=14.0, 2.4 Hz, 1H), 7.20 (t, J=9.2 Hz, 1H), 7.09-7.05 (m, 1H), 6.42 (d, J=4.8 Hz, 1H), 6.22 (t, J=5.6 Hz, 1H), 3.84-3.72 (m, 5H), 3.63-3.58 (m, 2H), 3.01-2.94 (m, 2H), 2.86 (s, 2H), 2.59-2.50 (m, 1H), 0.97 (t, J=7.2 Hz, 3H), 0.61-0.56 (m, 2H), 0.45-0.40 (m, 2H). MS (m/z): 634.60 (M+H).

Workup

  1. concentrationThe mixture was then concentrated
  2. additiondiluted with water
  3. additionthe pH was adjusted to 6-7 by addition of 1N HCl
  4. additionTo the resulting suspension was added MeOH
  5. dissolutionto dissolve the mixture clearly
  6. custompurified via Biotage [KP-C18-HS 30 g, gradient 20-95% (methanol/water)]

Sources & evidence

ORD record
ord-bf56df3051674db3bd442b58cb31c66f
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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