Sodium Bicarbonate → HCID 67441492, compound

HRID 1400890Notes

Reaction equation

HRID 1400890 reaction equation
Cl.Cl.[CH:3]1([NH:6][C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]4[CH:23]=[C:24]([C:26]5[CH2:27][CH2:28][NH:29][CH2:30][CH:31]=5)[S:25][C:18]=34)=[C:12]([F:32])[CH:11]=2)=[O:8])[CH2:5][CH2:4]1.C([O-])(O)=O.[Na+]>CCOC(C)=O>[CH:3]1([NH:6][C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]4[CH:23]=[C:24]([C:26]5[CH2:27][CH2:28][NH:29][CH2:30][CH:31]=5)[S:25][C:18]=34)=[C:12]([F:32])[CH:11]=2)=[O:8])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67442257HCID 67442257, compound

Product 1

HCID 67441492HCID 67441492, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the dihydrochloride 271 (150 mg, 0.302 mmol) in EtOAc (50 mL) was added a saturated solution of NaHCO3 (50 mL). The reaction mixture was stirred for 1 h to give a suspension. The solid was collected by filtration, rinsed with water, dried under vacuum and purified by Biotage (SNAP 25 g cartridge; 2% of ammonium hydroxide in MeOH/DCM: 0/100 to 15/85 over 20 CV) to produce a material that upon trituration with AcOEt afforded the title compound 271-A (45 mg, 0.106 mmol, 35% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.75 (s, 1H), 8.43 (d, =5.6 Hz, 1H), 7.71 (dd, J=2.0 and 13.6 Hz, 1H), 7.47 (s, 1H), 7.34 (t, J=9.2 Hz, 1H), 7.23-7.16 (m, 1H), 6.62 (s, 1H), 6.55 (d, J=5.6 Hz, 1H), 6.43 (s, 1H), 3.40 (bs, 2H), 2.93 (t, J=5.6 Hz, 2H), 2.59-2.50 (m, 1H), 2.46 (bs, 2H), 0.66-0.62 (m, 2H), 0.44-0.40 (m, 2H). MS (m/z): 425.42 (M+H)

Workup

  1. customto give a suspension
  2. filtrationThe solid was collected by filtration
  3. washrinsed with water
  4. customdried under vacuum
  5. custompurified by Biotage (SNAP 25 g cartridge; 2% of ammonium hydroxide in MeOH/DCM: 0/100 to 15/85 over 20 CV)
  6. customto produce a material that upon trituration with AcOEt

Sources & evidence

ORD record
ord-f469f3f167574719945292a1f66db10c
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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