Ethyl chloroformate → HCID 25169550, compound

HRID 881797Notes

Reaction equation

HRID 881797 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:29])[N:6]2[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:18]=1.C(N(CC)C(C)C)(C)C.[CH2:39]([O:41][C:42](Cl)=[O:43])[CH3:40]>ClCCl>[C:42](=[O:43])([O:41][CH2:39][CH3:40])[O:29][C:5]1[N:6]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][N:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)[CH:18]=2)[C:7]2[C:3]([N:4]=1)=[C:2]([NH2:1])[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=2

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 178496188HCID 178496188, compound

Product 1

HCID 25169550HCID 25169550, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6-Amino-2-(2-methoxy-ethoxy)-9-(3-pyrrolidin-1-ylmethyl-benzyl)-9H-purin-8-ol (Example A) (60 mg, 0.15 mmol) was dissolved in dichloromethane (2 mL). N,N-diisopropylethylamine (0.1 mL) was added and the mixture was cooled to 0° C. Ethylchloroformate (0.04 mL, 0.42 mmol) was added. After stirring for 30 minutes, the reaction was quenched with water and concentrated under vacuum. Purification by preparative reverse phase HPLC (5-45% acetonitrile/40 mM aqueous HCl) gave 9-(3-(pyrrolidin-1-ylmethyl)benzyl)-6-amino-2-(2-methoxyethoxy)-9H-purin-8-yl ethyl carbonate (Example Q) (24 mg) as a white glassy solid, HCl salt.

Workup

  1. customthe reaction was quenched with water
  2. concentrationconcentrated under vacuum
  3. customPurification by preparative reverse phase HPLC (5-45% acetonitrile/40 mM aqueous HCl)

Sources & evidence

ORD record
ord-671c8189b54c49a190a2a4176624cd0b
Source dataset
uspto-grants-2015_03
Patent number
US08993755B2

Reaction notes

Loading…