Trifluoroacetic acid → HCID 46913172, compound

HRID 1626604Notes

Reaction equation

HRID 1626604 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([NH:10][C:11](=[O:40])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[C:21]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][C@@H:34]3[CH3:39])[C:22]3[CH2:27][N:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:25][C:23]=3[N:24]=2)=[CH:15][CH:14]=1)[CH3:9].FC(F)(F)C(O)=O.CCN(C(C)C)C(C)C.ClC(OCC)=O>O1CCOCC1>[CH2:8]([NH:10][C:11](=[O:40])[NH:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:20]=[C:21]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][C@@H:34]3[CH3:39])[C:22]3[CH2:27][N:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:25][C:23]=3[N:24]=2)=[CH:17][CH:18]=1)[CH3:9]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 86663158HCID 86663158, compound

Product 1

HCID 46913172HCID 46913172, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-ethyl 2-(4-(3-ethylureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate trifluoroacetate (example 7 as a trifluoroacetic acid salt) (155 mg, 0.25 mmol) in dioxane (4 mL) at room temperature (20° C.) was added DIPEA (22 uL, 0.26 mmol) followed by ethyl chloroformate (24 uL, 0.25 mmol). The reaction mixture was stirred for 3 h. The solvent was removed in vacuo and the residue purified by prep HPLC (low pH) to afford a brown solid (36 mg, 32%).

Workup

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

Sources & evidence

ORD record
ord-90d12f74579d480ebf2e1e433c7742d5
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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