Propyl chloroformate → HCID 86669257, compound

HRID 2366918Notes

Reaction equation

HRID 2366918 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH2:27])[CH2:6][C@@H:5]1[CH2:28][CH3:29])(=[O:3])[CH3:2].CCN(C(C)C)C(C)C.[CH2:39]([O:42][C:43](Cl)=[O:44])[CH2:40][CH3:41]>ClCCl>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:27][C:43](=[O:44])[O:42][CH2:39][CH2:40][CH3:41])[CH2:6][C@@H:5]1[CH2:28][CH3:29])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7998Propyl chloroformateHCID 81531DiisopropylethylamineHCID 67193937HCID 67193937, compound

Product 1

HCID 86669257HCID 86669257, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(cis)-1-Acetyl-2-ethyl-6-[4-(1-piperidinylmethyl)phenyl]-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see Intermediate 5) (50 mg, 0.128 mmol) was dissolved in dichloromethane (DCM) (2 mL), mixed with DIPEA (0.045 mL, 0.255 mmol) and propylchloroformate (0.019 mL, 0.166 mmol, Aldrich) and stirred under nitrogen. After 40 minutes the reaction was loaded onto a 5 g SCX-column, eluting with MeOH (70 mL) followed by 2M MeOH/NH3 (70 mL). Product-containing fractions were evaporated to dryness to give a colourless solid (38 mg). This was purified on a 12+M Biotage silica column, eluting with 0 to 8% 2M methanolic ammonia in DCM. Product-containing fractions were evaporated to dryness to give a clear, colourless solid (16 mg). LCMS (Method C): Rt=0.83, MH+=478

Workup

  1. washSCX-column, eluting with MeOH (70 mL)
  2. customProduct-containing fractions were evaporated to dryness

Sources & evidence

ORD record
ord-861a802d620840c1a04926eae22bccd8
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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