Diisopropylethylamine → HCID 86710212, compound

HRID 2168217Notes

Reaction equation

HRID 2168217 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]#[N:12])=[CH:9][N:8]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH:21]1[CH2:26][CH2:25][CH:24]([NH:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:23][CH2:22]1.C(N(CC)C(C)C)(C)C>CN1C(=O)CCC1>[C:11]([C:10]1[C:3]2[C:2]([N:21]3[CH2:26][CH2:25][CH:24]([NH:27][C:28](=[O:35])[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:23][CH2:22]3)=[N:7][CH:6]=[N:5][C:4]=2[N:8]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:9]=1)#[N:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 118120N-4-PiperidylbenzamideHCID 86710211HCID 86710211, compound

Product 1

HCID 86710212HCID 86710212, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-chloro-7-({[2-(trimethylsilyl)ethyl]oxy}methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile D43 (100 mg) and N-4-piperidinylbenzamide (86 mg, 0.42 mmol, commercially available from e.g. Fluorochem, Alfa Aesar and Apollo) were dissolved in NMP and then N,N-diisopropylethylamine was added dropwise. The reaction mixture was carried out in the microwave at 120° C. for 45 minutes. The reaction mixture was poured onto water extracted with EtOAc (2×60 ml). Organic layers were washed water (3×20 ml), brine (30 ml), dried (MgSO4), filtered and solvent removed. Crude product obtained was purified by flash chromatography on silica gel eluting with Pet Eth/EtOAc 3/1-2/1 to give the desired product D44 in 69 mg. LCMS [MH+] [email protected] min (5 min run)

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionextracted with EtOAc (2×60 ml)
  3. washOrganic layers were washed water (3×20 ml), brine (30 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customsolvent removed
  7. customCrude product obtained
  8. customwas purified by flash chromatography on silica gel eluting with Pet Eth/EtOAc 3/1-2/1

Sources & evidence

ORD record
ord-ddff8e099e714544a241e07cc5d67ab1
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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