Triethylamine → HCID 69005605, compound

HRID 2367048Notes

Reaction equation

HRID 2367048 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH:13]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][C@H:18]([NH2:21])[CH2:17]3)=[O:15])[N:11]=[CH:10]2)[CH:4]=1.[OH:24][C:25]1([C:32]2[CH:33]=[N:34][C:35]([C:38]3[N:43]=[CH:42][CH:41]=[CH:40][N:39]=3)=[CH:36][CH:37]=2)[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C>C(Cl)Cl.CCOC(C)=O>[N:39]1[CH:40]=[CH:41][CH:42]=[N:43][C:38]=1[C:35]1[N:34]=[CH:33][C:32]([C:25]2([OH:24])[CH2:30][CH2:29][CH:28]([NH:21][C@H:18]3[CH2:19][CH2:20][N:16]([C:14]([C:12]4[N:11]=[CH:10][N:9]([C:5]5[CH:4]=[C:3]([C:2]([F:1])([F:22])[F:23])[CH:8]=[CH:7][N:6]=5)[CH:13]=4)=[O:15])[CH2:17]3)[CH2:27][CH2:26]2)=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57803357HCID 57803357, compoundHCID 69003439HCID 69003439, compound

Product 1

HCID 69005605HCID 69005605, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3S)-1-({1-[4-(trifluoromethyl)pyridin-2-yl]-1H-imidazol-4-yl}carbonyl)pyrrolidin-3-amine (50 mg, 0.15 mmol) and 4-hydroxy-4-(6-pyrimidin-2-ylpyridin-3-yl)cyclohexanone (41 mg, 0.15 mmol) in methylene chloride (3 mL) was added sodium triacetoxyborohydride (36 mg, 0.17 mmol) followed by triethylamine (0.086 mL, 0.61 mmol). After being stirred at room temperature for 2 h, EtOAc (50 mL) was added. The solution was washed with NaHCO3 solution and water, dried (MgSO4) and concentrated. Purification by HPLC provided two isomers. MS (M+H) 579.3 for both isomers.

Workup

  1. washThe solution was washed with NaHCO3 solution and water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customPurification by HPLC
  5. customprovided two isomers

Sources & evidence

ORD record
ord-df3217600c654c579f2944fa0b181a6c
Source dataset
uspto-grants-2014_04
Patent number
US08697870B2

Reaction notes

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