Ammonium Chloride → HCID 86648395, compound

HRID 409453Notes

Reaction equation

HRID 409453 reaction equation
[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[CH2:6][N:7]([C:27]1[N:32]=[CH:31][C:30]([C:33]2[CH:34]=[N:35][N:36]([CH3:38])[CH:37]=2)=[CH:29][N:28]=1)[C@@H:8]1[CH2:12][N:11]([C:13]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:14]=2[CH:15]=[O:16])[C@H:10]([CH2:25][CH3:26])[CH2:9]1.[CH3:48][Mg+].[Br-].[NH4+].[Cl-]>C1COCC1>[F:47][C:2]([F:46])([F:1])[C:3]1[CH:4]=[C:5]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[CH2:6][N:7]([C:27]1[N:28]=[CH:29][C:30]([C:33]2[CH:34]=[N:35][N:36]([CH3:38])[CH:37]=2)=[CH:31][N:32]=1)[C@@H:8]1[CH2:12][N:11]([C:13]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][C:14]=2[CH:15]([OH:16])[CH3:48])[C@H:10]([CH2:25][CH3:26])[CH2:9]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 59614338HCID 59614338, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 86648395HCID 86648395, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 2-((2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-5-trifluoromethyl-benzaldehyde (120 mg, 0.17 mmol) in THF (3 mL) is added MeMgBr (0.24 mL, 0.23 mmol) in THF solution (0.97M). The reaction mixture is stirred at room temperature for 0.5 hour. After addition of saturated NH4Cl aq., the mixture is extracted with EtOAc. The combined organic layer is dried over MgSO4 then concentrated under reduced pressure to give 1-[2-((2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-5-trifluoromethyl-phenyl]-ethanol as a colorless oil (122 mg, quant.). ESI-MS m/z: 687 [M+1]+, Retention time 2.05 min (condition A).

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. dry with materialThe combined organic layer is dried over MgSO4
  3. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-621be47825234a45b8b08e1c31307cfa
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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