Water → HCID 86723651, compound

HRID 1485313Notes

Reaction equation

HRID 1485313 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:11]4[CH2:28][CH2:27][CH2:26][C:12]=4[N:13]=[C:14]([N:16]4[CH2:20][C@H:19]([O:21][CH3:22])[CH2:18][CH:17]4[C:23]([OH:25])=[O:24])[N:15]=3)[CH:5]=2)[CH2:3][CH2:2]1.[CH:29]1C=CC2N(O)N=NC=2C=1.O.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl>CO>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:11]4[CH2:28][CH2:27][CH2:26][C:12]=4[N:13]=[C:14]([N:16]4[CH2:20][C@H:19]([O:21][CH3:22])[CH2:18][CH:17]4[C:23]([O:25][CH3:29])=[O:24])[N:15]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 962WaterHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86723652HCID 86723652, compound

Product 1

HCID 86723651HCID 86723651, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (4R)-1-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-4-methoxypyrrolidine-2-carboxylic acid (3.5 g, 9.11 mmol) in MeOH (20 mL) was added HOBt.H2O (2.27 g, 4.56 mmol), N-methylmorpholine (2 mL, 18.22 mmol) and EDCI.HCl (2.44 g, 12.75 mmol). The reaction mixture was allowed to stir at RT for 1 h. MeOH was removed under reduced pressure and the residue was dissolved in EtOAc (200 mL). The solution was washed with water (10×100 mL) followed by brine (100 mL) and dried over anhydrous sodium sulfate. Removal of EtOAc under reduced pressure afforded (4R)-methyl 1-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-4-methoxypyrrolidine-2-carboxylate (3 g).

Workup

  1. customMeOH was removed under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc (200 mL)
  3. washThe solution was washed with water (10×100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customRemoval of EtOAc under reduced pressure

Sources & evidence

ORD record
ord-764b46b49727478db81fff82e0e3018e
Source dataset
uspto-grants-2016_08
Patent number
US09422267B2

Reaction notes

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