4-Bromobutyryl chloride → HCID 178427997, compound

HRID 215958Notes

Reaction equation

HRID 215958 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[NH2:8][C:9]1[CH:10]=[C:11]([CH3:33])[C:12]([N:15]2[CH2:32][CH2:31][C:18]3([C:22](=[O:23])[N:21]([C@H:24]4[CH2:29][CH2:28][C@@H:27]([OH:30])[CH2:26][CH2:25]4)[CH2:20][CH2:19]3)[CH2:17][CH2:16]2)=[N:13][CH:14]=1.CC(C)([O-])C.[K+]>CN(C)C1C=CN=CC=1.ClCCl.O1CCCC1>[OH:30][C@@H:27]1[CH2:26][CH2:25][C@H:24]([N:21]2[CH2:20][CH2:19][C:18]3([CH2:31][CH2:32][N:15]([C:12]4[C:11]([CH3:33])=[CH:10][C:9]([N:8]5[CH2:2][CH2:3][CH2:4][C:5]5=[O:6])=[CH:14][N:13]=4)[CH2:16][CH2:17]3)[C:22]2=[O:23])[CH2:29][CH2:28]1

Participants

7

Reactant 3

HCID 702254-Bromobutyryl chlorideHCID 23665647Potassium tert-butoxideHCID 178428568HCID 178428568, compound

Product 1

HCID 178427997HCID 178427997, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Bromobutanoyl chloride (13.0 μL) was added to a mixture of 8-(5-amino-3-methylpyridin-2-yl)-2-(cis-4-hydroxycyclohexyl)-2,8-diazaspiro[4.5]decan-1-one (18.0 mg) and 4-dimethylaminopyridine (14.5 mg) in dichloromethane (1.0 mL). The mixture was stirred for 3 h. Then potassium tert-butoxide in tetrahydrofuran (1.0 M, 0.20 mL) was added. The mixture was stirred for an additional hour. The solvent was evaporated. The residue was dissolved in methanol (1.8 mL), and purified by prep.-HPLC under basic condition to afford 2-(cis-4-hydroxycyclohexyl)-8-[3-methyl-5-(2-oxopyrrolidin-1-yl)pyridin-2-yl]-2,8-diazaspiro[4.5]decan-1-one. LCMS: (M+H)+=427.20.

Workup

  1. stirringThe mixture was stirred for an additional hour
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in methanol (1.8 mL)
  4. custompurified by prep.-HPLC under basic condition

Sources & evidence

ORD record
ord-b55b1b8cb8c047d0a31a6298eebe6c9b
Source dataset
uspto-grants-2012_06
Patent number
US08193207B2

Reaction notes

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