(R)-2-Methylpyrrolidine → HCID 69674917, compound

HRID 575509Notes

Reaction equation

HRID 575509 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][NH:3]1.[F:7][CH:8]1[CH:13]([O:14][C:15]2[CH:20]=[C:19]([CH:21]=O)[CH:18]=[C:17]([F:23])[CH:16]=2)[CH2:12][CH2:11][N:10]([CH2:24][CH:25]([N:29]2[CH:33]=[C:32]([C:34]3[C:35]4[CH:42]=[CH:41][N:40](COCC[Si](C)(C)C)[C:36]=4[N:37]=[CH:38][N:39]=3)[CH:31]=[N:30]2)[CH2:26][C:27]#[N:28])[CH2:9]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:7][CH:8]1[CH:13]([O:14][C:15]2[CH:20]=[C:19]([CH2:21][N:3]3[CH2:4][CH2:5][CH2:6][C@H:2]3[CH3:1])[CH:18]=[C:17]([F:23])[CH:16]=2)[CH2:12][CH2:11][N:10]([CH2:24][CH:25]([N:29]2[CH:33]=[C:32]([C:34]3[C:35]4[CH:42]=[CH:41][NH:40][C:36]=4[N:37]=[CH:38][N:39]=3)[CH:31]=[N:30]2)[CH2:26][C:27]#[N:28])[CH2:9]1

Participants

5

Reactant 3

HCID 641544(R)-2-MethylpyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 86666558HCID 86666558, compound

Product 1

HCID 69674917HCID 69674917, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (2R)-2-methylpyrrolidine (2.3 μL, 0.023 mmol) and 4-[3-fluoro-4-(3-fluoro-5-formylphenoxy)piperidin-1-yl]-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}- 7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butanenitrile (13.5 mg, 0.0217 mmol) (diastereomer 2) in DCM (0.10 mL) was added resin of sodium triacetoxyborohydride (13 mg, 0.032 mmol). The resulting mixture was stirred overnight. The reaction solution was filtered, washed with additional DCM, and concentrated. The residue was purified with LCMS (C18 column eluting with a gradient of ACN/H2O containing 0.15% NH4OH) to give the desired product (3.4 mg, 23%). LCMS (M+H)+: 691.4.

Workup

  1. filtrationThe reaction solution was filtered
  2. washwashed with additional DCM
  3. concentrationconcentrated
  4. customThe residue was purified with LCMS (C18 column
  5. washeluting with a gradient of ACN/H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-35555387d00748318ce56622f5bb2fa6
Source dataset
uspto-grants-2015_05
Patent number
US09034884B2

Reaction notes

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