Methyl chloroformate → HCID 46913171, compound

HRID 1626603Notes

Reaction equation

HRID 1626603 reaction equation
Cl.[CH2:2]([NH:4][C:5](=[O:33])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][C@@H:27]3[CH3:32])[C:16]3[CH2:21][N:20]([C:22]([O:24][CH3:25])=[O:23])[CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)[CH3:3].CCN(C(C)C)C(C)C.ClC(OC)=O>O1CCOCC1>[CH2:2]([NH:4][C:5](=[O:33])[NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[C:15]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][C@@H:27]3[CH3:32])[C:16]3[CH2:21][N:20]([C:22]([O:24][CH3:25])=[O:23])[CH2:19][C:17]=3[N:18]=2)=[CH:11][CH:12]=1)[CH3:3]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66687860HCID 66687860, compound

Product 1

HCID 46913171HCID 46913171, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-methyl 2-(4-(3-ethylureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate hydrochloride (example 7 as a hydrochloride salt) (88 mg, 0.21 mmol) in dioxane (5 mL) at room temperature (20° C.) was added DIPEA (19 uL, 0.1 mmol) followed by methyl chloroformate (18 uL, 0.23 mmol). The reaction mixture was stirred overnight. The solvent was removed in vacuo and the residue purified by prep HPLC (low pH) to afford a brown solid (6 mg, 6%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by prep HPLC (low pH)

Sources & evidence

ORD record
ord-da93735a1f91443cb0aa1ad9917b0d34
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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