Ammonium Chloride → 3-[1-(6-Benzoyl-pyrimidin-4-yl)-piperidin-4-yl]-7-methoxy-1,3,4,5-tetrahydro-benzo[d]-[1,3]diazepin-2-one

HRID 469378Notes

Reaction equation

HRID 469378 reaction equation
CON(C)[C:4]([C:6]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:24][CH2:23][C:22]4[CH:25]=[C:26]([O:29][CH3:30])[CH:27]=[CH:28][C:21]=4[NH:20][C:19]3=[O:31])[CH2:14][CH2:13]2)[N:9]=[CH:8][N:7]=1)=[O:5].[C:33]1([Mg]Br)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[Cl-].[NH4+]>C1COCC1>[C:4]([C:6]1[N:7]=[CH:8][N:9]=[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:24][CH2:23][C:22]4[CH:25]=[C:26]([O:29][CH3:30])[CH:27]=[CH:28][C:21]=4[NH:20][C:19]3=[O:31])[CH2:14][CH2:13]2)[CH:11]=1)(=[O:5])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 581811336-[4-(7-Methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acidmethoxy-methyl-amideHCID 178418255HCID 178418255, compound2×

Product 1

HCID 252683833-[1-(6-Benzoyl-pyrimidin-4-yl)-piperidin-4-yl]-7-methoxy-1,3,4,5-tetrahydro-benzo[d]-[1,3]diazepin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

Under a nitrogen atmosphere 100 mg (0.227 mmol) 6-[4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acidmethoxy-methyl-amide were cooled to −10° C. in 5.00 mL THF and combined with 0.400 mL (0.400 mmol) phenylmagnesium bromide solution (1M in THF). The mixture was stirred for 1 h at −10° C. and then heated to 0° C. Then 0.200 mL (0.200 mmol) phenylmagnesium bromide solution (1M in THF) were added, the mixture was stirred for 1 h and then heated to RT. The reaction mixture was combined with a saturated ammonium chloride solution and extracted with EtOAc. The combined organic phases were dried and evaporated down i. vac. The residue was purified by preparative HPLC-MS. The fractions containing the product were combined and evaporated down by half. The precipitate formed was suction filtered and dried.

Workup

  1. temperatureheated to 0° C
  2. stirringthe mixture was stirred for 1 h
  3. temperatureheated to RT
  4. extractionextracted with EtOAc
  5. customThe combined organic phases were dried
  6. customevaporated down i
  7. customThe residue was purified by preparative HPLC-MS
  8. additionThe fractions containing the product
  9. customevaporated down by half
  10. customThe precipitate formed
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-d498ac6bfab34ea6afa8379d155e14e5
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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