Diethylamine → HCID 178464108, compound

HRID 2053013Notes

Reaction equation

HRID 2053013 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH2:16])[C:10]=3[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]=3)=[CH:8]2)[CH2:4]1.Cl[C:32]([O:34][CH2:35][CH2:36]Br)=[O:33].[CH2:38]([N:40](CC)[CH2:41][CH3:42])[CH3:39].C(NCC)C>ClCCl>[CH2:38]([N:40]([CH2:41][CH3:42])[CH2:36][CH2:35][O:34][C:32](=[O:33])[NH:1][CH2:2][C@H:3]1[CH2:4][C@H:5]([N:7]2[C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH2:16])[C:10]=3[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]=3)=[CH:8]2)[CH2:6]1)[CH3:39]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 8471TriethylamineHCID 785282-Bromoethyl chloroformateHCID 178511295HCID 178511295, compound

Product 1

HCID 178464108HCID 178464108, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.2 g (0.5 mmol) of trans-7-(3-aminomethyl-cyclobutyl)-5-(3-benzyloxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine in 5 ml of dichloromethane are added 55.4 μl (0.5 mmol) of 2-bromoethyl chloroformate (Fluka, Buchs, Switzerland) and 70 μl (0.5 mmol) of triethylamine. After stirring for 2 h at RT, the solution is concentrated to dryness. The crude compound is dissolved in 5 ml of acetonitrile and 260 μl (2.5 mmol) of diethylamine (Fluka, Buchs, Switzerland) are added thereto. The reaction mixture is refluxed for 16 h and, after concentration, the crude compound is purified by medium-pressure liquid chromatography to provide trans-{3-[4-amino-5-(3-benzyloxy-phenyl)pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutylmethyl}-carbamic acid 2-diethylamino-ethyl ester. Analytical HPLC: tR=6.27 min (Grad 2); ES-MS: m/eo=543.3.

Workup

  1. concentrationthe solution is concentrated to dryness
  2. dissolutionThe crude compound is dissolved in 5 ml of acetonitrile
  3. temperatureThe reaction mixture is refluxed for 16 h
  4. concentrationafter concentration
  5. customthe crude compound is purified by medium-pressure liquid chromatography

Sources & evidence

ORD record
ord-63f93b1ce64e4b7c961ecdd9ed8a52ac
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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