Triethylamine → HCID 46913369, compound

HRID 1626555Notes

Reaction equation

HRID 1626555 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:22]3[CH2:27][CH2:26][O:25][CH2:24][C@@H:23]3[CH3:28])[C:16]3[CH2:21][NH:20][CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>CC#N>[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:22]3[CH2:27][CH2:26][O:25][CH2:24][C@@H:23]3[CH3:28])[C:16]3[CH2:21][N:20]([S:37]([CH3:36])(=[O:39])=[O:38])[CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 46913468HCID 46913468, compound

Product 1

HCID 46913369HCID 46913369, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea (example 7) (60 mg, 0.16 mmol) in MeCN (1.5 mL) was added triethylamine (64 uL, 0.47 mmol) and methane sulfonyl chloride (36 uL, 0.47 mmol). The reaction mixture was stirred overnight at room temperature and concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The organic layer was concentrated and the product isolated by Prep HPLC (low pH) as an off white/pink solid (36 mg, 0.078 mmol, 49% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between water and ethyl acetate
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-c20e3b007f73474db78dec56da3c0771
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

Loading…