Ammonium Chloride → HCID 57886962, compound

HRID 1819328Notes

Reaction equation

HRID 1819328 reaction equation
[Cl:1][C:2]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:3]=1[CH2:4][N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH3:15])[C:10](S(C)(=O)=O)=[N:9][C:8]=2[C:7]([C:20]#[N:21])=[C:6]1[N:22]1[CH2:27][CH2:26][CH2:25][C@@H:24]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:23]1.[CH3:41][Mg]Br.C(OCC)C.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:3]=1[CH2:4][N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH3:15])[C:10]([CH3:41])=[N:9][C:8]=2[C:7]([C:20]#[N:21])=[C:6]1[N:22]1[CH2:27][CH2:26][CH2:25][C@@H:24]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:23]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 57886996tert-butyl {(3R)-1-[5-(2-chloro-5-fluorobenzyl)-7-cyano-3-methyl-2-(methylsulfonyl)-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamateHCID 178467822HCID 178467822, compound

Product 1

HCID 57886962HCID 57886962, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl {(3R)-1-[5-(2-chloro-5-fluorobenzyl)-7-cyano-3-methyl-2-(methylsulfonyl)-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate (890 mg) in tetrahydrofuran (2 ml) was cooled to 0° C. and a 3M methylmagnesium bromide/diethyl ether solution (333 μl) was added dropwise thereto. After 30 minutes, the reaction solution was warmed to room temperature and stirred for 1 hour. A saturated aqueous ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate (100 ml). The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and then filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain the title compound (64 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate (100 ml)
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-77f8844ed5af49c89c3a6e9bbb1edad0
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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