Methyl chloroformate → HCID 66679193, compound

HRID 1626636Notes

Reaction equation

HRID 1626636 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][C@@H:29]3[CH3:34])[C:16]3[CH2:21][N:20]([CH:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)[CH2:19][C:17]=3[N:18]=2)=[CH:9][C:8]=1[F:35])=[O:5])[CH3:2].CCN(C(C)C)C(C)C.Cl[C:46]([O:48][CH3:49])=[O:47]>O1CCOCC1>[CH2:1]([NH:3][C:4](=[O:5])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][C@@H:29]3[CH3:34])[C:16]3[CH2:21][N:20]([CH:22]4[CH2:23][CH2:24][N:25]([C:46]([O:48][CH3:49])=[O:47])[CH2:26][CH2:27]4)[CH2:19][C:17]=3[N:18]=2)=[CH:9][C:8]=1[F:35])[CH3:2]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66687843HCID 66687843, compound

Product 1

HCID 66679193HCID 66679193, compoundYield 5.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of (S)-1-ethyl-3-(2-fluoro-4-(4-(3-methylmorpholino)-6-(piperidin-4-yl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea (90 mg, 0.17 mmol) and DIPEA (30 μL, 0.17 mmol) in Dioxane (5 mL) was added methyl chloroformate (14 μL, 0.19 mmol). Reaction mixture was stirred at room temperature until analysis by LCMS indicated reaction was complete. Solvent was then removed in vacuo. Purified by prep. HPLC (low pH) to afford an orange gum. This was then further purified using a TsOH cartridge to remove residual formic acid from HPLC (loaded in MeOH eluted with 2M methanolic ammonia). This gave a creamy pink solid (4.9 mg, 0.009 mmol, 5.3%).

Workup

  1. customReaction mixture
  2. customreaction
  3. customSolvent was then removed in vacuo
  4. customPurified by prep
  5. customHPLC (low pH) to afford an orange gum
  6. customThis was then further purified
  7. customto remove residual formic acid
  8. washfrom HPLC (loaded in MeOH eluted with 2M methanolic ammonia)

Sources & evidence

ORD record
ord-6e9de7e3255641f7b91b6110a52e800b
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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