Lithium Hydroxide → HCID 178510020, compound

HRID 1639999Notes

Reaction equation

HRID 1639999 reaction equation
C([O:9][C@H:10]1[CH2:15][CH2:14][C@@H:13]([N:16]2[CH2:20][CH2:19][C@:18]3([CH2:25][CH2:24][CH2:23][NH:22][CH2:21]3)[C:17]2=[O:26])[CH2:12][CH2:11]1)(=O)C1C=CC=CC=1.Cl[C:28]1[N:35]=[CH:34][CH:33]=[CH:32][C:29]=1[C:30]#[N:31].C(N(CC)C(C)C)(C)C.CN1CCCC1=O.[OH-].[Li+]>CO>[OH:9][C@@H:10]1[CH2:11][CH2:12][C@H:13]([N:16]2[CH2:20][CH2:19][C@:18]3([CH2:25][CH2:24][CH2:23][N:22]([C:28]4[N:35]=[CH:34][CH:33]=[CH:32][C:29]=4[C:30]#[N:31])[CH2:21]3)[C:17]2=[O:26])[CH2:14][CH2:15]1

Participants

7

Reactant 5

HCID 3939Lithium HydroxideHCID 13387N-methyl-2-pyrrolidoneHCID 810792-ChloronicotinonitrileHCID 81531DiisopropylethylamineHCID 178525737HCID 178525737, compound

Product 1

HCID 178510020HCID 178510020, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of cis-4-[(5S)-1-oxo-2,7-diazaspiro[4.5]dec-2-yl]cyclohexyl benzoate (19.0 mg, 0.0000533 mol), 2-chloronicotinonitrile (8.12 mg, 0.0000586 mol) and N,N-diisopropylethylamine (20.0 μL, 0.000115 mol) in N-methylpyrrolidinone (0.6 mL, 0.006 mol) was irradiated by microwave at 180° C. for 20 min. After cooling to rt, lithium hydroxide aqueous solution (1.0 M, 0.150 mL) was added, followed by methanol (0.2 mL). The mixture was heated at 100° C. for 5 h. The crude reaction mixture was then purified by prep-HPLC under basic conditions to afford the desired product. LC-MS: 355.2 (M+H)+.

Workup

  1. customwas irradiated by microwave at 180° C. for 20 min
  2. temperatureThe mixture was heated at 100° C. for 5 h
  3. customThe crude reaction mixture
  4. customwas then purified by prep-HPLC under basic conditions

Sources & evidence

ORD record
ord-5ed0e31ed2684dfbb0e2d9353dd5a86b
Source dataset
uspto-grants-2012_02
Patent number
US08110581B2

Reaction notes

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