1,2-Dichloroethane → (S)-4-(2-(4-(3-cyclopropylureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)-4-oxobutanamide

HRID 1626640Notes

Reaction equation

HRID 1626640 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[C:16]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]4[CH3:29])[C:17]4[CH2:22][NH:21][CH2:20][C:18]=4[N:19]=3)=[CH:10][CH:9]=2)=[O:6])[CH2:3][CH2:2]1.CN1CCOCC1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:51][C:52](=[O:58])[CH2:53][CH2:54][C:55](O)=[O:56]>CN(C=O)C>[CH:1]1([NH:4][C:5](=[O:6])[NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]3[N:15]=[C:16]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]4[CH3:29])[C:17]4[CH2:22][N:21]([C:55](=[O:56])[CH2:54][CH2:53][C:52]([NH2:51])=[O:58])[CH2:20][C:18]=4[N:19]=3)=[CH:12][CH:13]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 12522Succinamic acidHCID 757711-HydroxybenzotriazoleHCID 46894114(S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea

Product 1

HCID 66679041(S)-4-(2-(4-(3-cyclopropylureido)phenyl)-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)-4-oxobutanamideYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea (Example 3) (100 mg, 0.25 mmol) and N-methylmorpholine (56 μL, 0.5 mmol) in DMF (5 ml, anhydrous) was added EDC (53 mg, 0.28 mmol), HOBT (38 mg, 0.28 mmol), and 4-amino-4-oxobutanoic acid (29.7 mg, 0.25 mmol). The reaction mixture was stirred at room temperature until analysis by LCMS deemed reaction complete. Solvent was then removed in vacuo. Purified by prep. HPLC (high pH) to afford a white solid (25.7 mg, 0.052 mmol, 21%).

Workup

  1. customreaction complete
  2. customSolvent was then removed in vacuo
  3. customPurified by prep

Sources & evidence

ORD record
ord-6b1c26dd87de437599cba73a6330acd8
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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