Isopropyl chloroformate → HCID 57496301, compound

HRID 1864162Notes

Reaction equation

HRID 1864162 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:12]1[C:16]2=[N:17][CH:18]=[N:19][C:20]([NH:21][CH:22]3[CH2:26][CH2:25][NH:24][CH2:23]3)=[C:15]2[CH:14]=[N:13]1.[CH:27]([O:30][C:31](Cl)=[O:32])([CH3:29])[CH3:28].C(N(CC)CC)C>CN(C=O)C>[CH:27]([O:30][C:31]([N:24]1[CH2:25][CH2:26][CH:22]([NH:21][C:20]2[N:19]=[CH:18][N:17]=[C:16]3[N:12]([C:3]4[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:9])=[O:10])=[CH:7][C:2]=4[F:1])[N:13]=[CH:14][C:15]=23)[CH2:23]1)=[O:32])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 21897475HCID 21897475, compound

Product 1

HCID 57496301HCID 57496301, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of [1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-pyrrolidin-3-yl-amine (20 mg, 0.048 mmol), isopropylchloroformate (7.2 μL, 0.52 mmol), and triethylamine (20 μL, 0.144 mmol) in DMF (500 μL) was stirred for 2 hours at room temperature. The reaction was purified by HPLC to afford compound A142 as a white solid (9 mg, 41%). Exact mass calculated for C20H23FN6O4S 462.15 found 463.3 (MH+).

Workup

  1. customThe reaction was purified by HPLC

Sources & evidence

ORD record
ord-aae93066ed854162ab704c62b707e2e9
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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