Sodium Hydroxide → HCID 67441980, compound

HRID 1400936Notes

Reaction equation

HRID 1400936 reaction equation
[CH:1]1([NH:4][C:5](=[O:45])[NH:6][C:7]2[CH:43]=[CH:42][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]6[CH2:33][CH2:32][CH:31]([N:34]([CH3:41])[CH2:35][C:36]([O:38]CC)=[O:37])[CH2:30][CH2:29]6)=[CH:23][CH:22]=5)[S:20][C:13]=34)=[C:9]([F:44])[CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([NH:4][C:5](=[O:45])[NH:6][C:7]2[CH:43]=[CH:42][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]6[CH2:29][CH2:30][CH:31]([N:34]([CH3:41])[CH2:35][C:36]([OH:38])=[O:37])[CH2:32][CH2:33]6)=[CH:23][CH:22]=5)[S:20][C:13]=34)=[C:9]([F:44])[CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67443356HCID 67443356, compound

Product 1

HCID 67441980HCID 67441980, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 422 (78 mg, 0.12 mmol) in MeOH (3 mL) was added 1N NaOH (0.6 mL, 0.6 mmol). The reaction mixture was stirred at RT for 2 h. The reaction mixture was then concentrated, diluted with water and the pH was adjusted to 6-7 by addition of 1N HCl. The resulting suspension was stirred for 30 min, and the solid was collected by filtration, rinsed with water, air-dried and dried under high vacuum to afford the title compound 423 (50.3 mg, 67% yield) as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.81 (s, 1H), 8.55 (brd, 1H), 8.51 (d, J=5.6 Hz, 1H), 8.33 (s, 1H), 8.24 (d, J=8.0 Hz, 1H), 7.85 (dd, J=8.2, 2.0 Hz, 1H), 7.73 (dd, J=13.6, 2.4 Hz, 1H), 7.38 (t, J=9.0 Hz, 1H), 7.24-7.18 (m, 1H), 6.59-6.42 (m, 2H), 3.56 (s, 2H), 3.26 (s, 2H), 2.93-2.84 (m, 3H), 2.58-2.51 (m, 1H), 2.53 (s, 3H), 2.06-1.95 (m, 2H), 1.88-1.80 (m, 2H), 1.61-1.49 (m, 2H), 0.68-0.62 (m, 2H), 0.47-0.41 (m, 2H). MS (m/z): 605.59 (M+H).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additiondiluted with water
  3. additionthe pH was adjusted to 6-7 by addition of 1N HCl
  4. stirringThe resulting suspension was stirred for 30 min
  5. filtrationthe solid was collected by filtration
  6. washrinsed with water
  7. customair-dried
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-0932a5402dac48d2b94f64085009c0aa
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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