Isopropyl chloroformate → HCID 70674231, compound

HRID 1747721Notes

Reaction equation

HRID 1747721 reaction equation
Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].Cl.Cl.Cl.[F:11][C:12]1[CH:36]=[CH:35][CH:34]=[CH:33][C:13]=1[CH2:14][C:15]1[N:19]2[N:20]=[CH:21][CH:22]=[CH:23][C:18]2=[C:17]([C:24]2[N:29]=[C:28]([NH2:30])[C:27]([NH2:31])=[C:26]([NH2:32])[N:25]=2)[N:16]=1>N1C=CC=CC=1>[CH:2]([OH:4])=[O:3].[NH2:32][C:26]1[C:27]([NH:31][C:2](=[O:3])[O:4][CH:5]([CH3:7])[CH3:6])=[C:28]([NH2:30])[N:29]=[C:24]([C:17]2[N:16]=[C:15]([CH2:14][C:13]3[CH:33]=[CH:34][CH:35]=[CH:36][C:12]=3[F:11])[N:19]3[C:18]=2[CH:23]=[CH:22][CH:21]=[N:20]3)[N:25]=1

Participants

4

Reactant 2

HCID 7917Isopropyl chloroformateHCID 86716493HCID 86716493, compound

Product 1

HCID 70674231HCID 70674231, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

At 0° C., twice at an interval of 10 minutes, in each case 76.4 mg (0.62 mmol) of isopropyl chloroformate were added to 247 mg (0.62 mmol) of 2-[7-(2-fluorobenzyl)imidazo[1,5-b]pyridazin-5-yl]pyrimidine-4,5,6-triamine (Example 9A) in 4.9 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 189 mg (63% 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-e84cf5618d41471189985ae074d2b7e5
Source dataset
uspto-grants-2015_10
Patent number
US09150580B2

Reaction notes

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