Cyclopentyl chloroformate → HCID 70674345, compound

HRID 1747722Notes

Reaction equation

HRID 1747722 reaction equation
[C:1](Cl)(=[O:8])[O:2][CH:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1.Cl.Cl.Cl.[F:13][C:14]1[CH:38]=[CH:37][CH:36]=[CH:35][C:15]=1[CH2:16][C:17]1[N:21]2[N:22]=[CH:23][CH:24]=[CH:25][C:20]2=[C:19]([C:26]2[N:31]=[C:30]([NH2:32])[C:29]([NH2:33])=[C:28]([NH2:34])[N:27]=2)[N:18]=1>N1C=CC=CC=1>[CH:1]([OH:8])=[O:2].[NH2:34][C:28]1[C:29]([NH:33][C:1](=[O:8])[O:2][CH:3]2[CH2:7][CH2:6][CH2:5][CH2:4]2)=[C:30]([NH2:32])[N:31]=[C:26]([C:19]2[N:18]=[C:17]([CH2:16][C:15]3[CH:35]=[CH:36][CH:37]=[CH:38][C:14]=3[F:13])[N:21]3[C:20]=2[CH:25]=[CH:24][CH:23]=[N:22]3)[N:27]=1

Participants

4

Reactant 2

HCID 2735892Cyclopentyl chloroformateHCID 86716493HCID 86716493, compound

Product 1

HCID 70674345HCID 70674345, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

At 0° C., 37.5 mg (0.25 mmol) of cyclopentyl chlorocarbonate were added to 100 mg (0.25 mmol) of 2-[7-(2-fluorobenzyl)imidazo[1,5-b]pyridazin-5-yl]pyrimidine-4,5,6-triamine (Example 9A) in 2 ml of pyridine. The reaction mixture was concentrated and the residue was purified by preparative HPLC (acetonitrile:water (+0.1% formic acid) gradient). This gave 41 mg (32% of theory) of the target compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by preparative HPLC (acetonitrile:water (+0.1% formic acid) gradient)

Sources & evidence

ORD record
ord-e62c7099e4474d3b9fe9776ea37946e8
Source dataset
uspto-grants-2015_10
Patent number
US09150580B2

Reaction notes

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