Sodium Methoxide → HCID 178522293, compound

HRID 2168252Notes

Reaction equation

HRID 2168252 reaction equation
[Cl:1][C:2]1[C:10]2[C:9]([N:11]3[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:25])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:13][CH2:12]3)=[N:8][CH:7]=[N:6][C:5]=2[N:4](S(C2C=CC=CC=2)(=O)=O)[CH:3]=1.C[O-].[Na+]>CO>[Cl:1][C:2]1[C:10]2[C:5]([NH:6][CH:7]=[N:8][C:9]=2[N:11]2[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:13][CH2:12]2)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67988083HCID 67988083, compound

Product 1

HCID 178522293HCID 178522293, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

N-{1-[5-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-4-piperidinyl}benzamide D41 (240 mg) and sodium methoxide (157 mg, 2.9 mmol) were dissolved in MeOH (15 ml). The reaction mixture was heated at 75° C. for 30 min and then extracted with EtOAc (150 ml); washed with water (60 ml), brine (2×60 ml). Yellow oil obtained, solvent removed to afford a yellow solid which was purified by prep HPLC (mobile phase: A: 0.01% NH4HCO3/H2O B; ACN. Column shimazu PRC-ODS 10.0 uM, 20×250 mm. Method 07.8 min 40-50% ACN 8-10 min 95˜95% ACN. Flow rate 30 mL/min to give product E44 as an ashen solid in 73 mg. LCMS [MH+] [email protected] min (5 min run)

Workup

  1. extractionextracted with EtOAc (150 ml)
  2. washwashed with water (60 ml), brine (2×60 ml)
  3. customYellow oil obtained
  4. customsolvent removed
  5. customto afford a yellow solid which
  6. customwas purified by prep HPLC (mobile phase
  7. customMethod 07.8 min 40-50% ACN 8-10 min 95˜95% ACN
  8. customFlow rate 30 mL/min to give product E44 as an ashen solid in 73 mg
  9. customLCMS [MH+] [email protected] min (5 min run)

Sources & evidence

ORD record
ord-1551c8d0260d4171958e3ba68092b76c
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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