Ammonium Chloride → HCID 59618687, compound

HRID 1691476Notes

Reaction equation

HRID 1691476 reaction equation
[OH:1][C:2]([C:9]1[CH:10]=[CH:11][C:12]2[NH:18][C:17]3[N:19]=[C:20]([C:23]([F:26])([F:25])[F:24])[CH:21]=[CH:22][C:16]=3[CH2:15][N:14]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:13]=2[CH:41]=1)([CH3:8])[C:3]([O:5]CC)=[O:4].O=C(C1C=CC2NC3N=C(C(F)(F)F)C=CC=3CN(S(C3C=CC(OC(F)(F)F)=CC=3)(=O)=O)C=2C=1)C(OCC)=O.C[Mg+].[Br-].[NH4+].[Cl-].C([O-])(O)=O.[Na+]>C1COCC1.C1(C)C=CC=CC=1>[OH:1][C:2]([C:9]1[CH:10]=[CH:11][C:12]2[NH:18][C:17]3[N:19]=[C:20]([C:23]([F:25])([F:26])[F:24])[CH:21]=[CH:22][C:16]=3[CH2:15][N:14]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([O:36][C:37]([F:38])([F:40])[F:39])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:13]=2[CH:41]=1)([CH3:8])[C:3]([OH:5])=[O:4]

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 59618637HCID 59618637, compoundHCID 59618805HCID 59618805, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 59618687HCID 59618687, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-hydroxy-2-[6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]propanoate To a solution of ethyl oxo[6-{[4-(trifluoro-methoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]acetate (103 mg, 0.175 mmol, Example 510) in THF was added a solution of MeMgBr (0.25 ml, 0.35 mmol) in toluene (1.4 M) and the solution was stirred for 30 min. at 0° C. The LC-MS showed the reaction was almost complete. The solution was poured into aqueous NH4Cl to quench the reaction, and the pH was adjusted to 7-8 with 1N aqueous NaHCO3. The mixture was partitioned between 20 mL of CH2Cl2 and 5 mL of water, and the aqueous layer was extracted with CH2Cl2 (2×20 mL). The combined organic layers were dried over Na2SO4, and the solvent was evaporated under reduced pressure to give the title compound as white solid; Mass Spectrum: m/e=606 (M+1).

Workup

  1. customto quench
  2. customthe reaction
  3. customThe mixture was partitioned between 20 mL of CH2Cl2 and 5 mL of water
  4. extractionthe aqueous layer was extracted with CH2Cl2 (2×20 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2ccf7946a6a14b3b9e2daa3088b1f2a8
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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