Dichloromethane → HCID 59239592, compound

HRID 1698013Notes

Reaction equation

HRID 1698013 reaction equation
[CH2:1]([NH:3][C:4](=[O:38])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][C@@H:32]3[CH3:37])[C:15]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[C:18]([CH3:30])([CH3:29])[C:16]=3[N:17]=2)=[CH:8][CH:7]=1)[CH3:2].C(Cl)Cl.FC(F)(F)C(O)=O>>[CH3:30][C:18]1([CH3:29])[C:16]2[N:17]=[C:12]([C:9]3[CH:10]=[CH:11][C:6]([NH:5][C:4]([NH:3][CH2:1][CH3:2])=[O:38])=[CH:7][CH:8]=3)[N:13]=[C:14]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][C@@H:32]3[CH3:37])[C:15]=2[CH2:21][CH2:20][NH:19]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 67179697HCID 67179697, compound

Product 1

HCID 59239592HCID 59239592, compound

Procedure

Step 2—Synthesis of compound wa: (S)-tert-butyl 2-(4-(3-ethylureido)phenyl)-8,8-dimethyl-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate (0.0861 g, 0.000164 mol) in Methylene chloride (2.00 mL, 0.0312 mol) was added Trifluoroacetic Acid (0.38 mL, 0.0049 mol). The reaction mixture was stirred for 1 hour. The reaction mixture was concentrated, diluted with sat NaHCO3, extracted three times with 10% MeOH in dichloromethane, dried over Magnesium sulfate, filtered, concentrated, and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.66 (s, 1H), 8.19 (d, J=8.8, 2H), 7.48 (d, J=8.8, 2H), 6.17 (t, J=5.5, 1H), 4.02 (d, J=6.9, 1H), 3.86 (d, J=11.1, 1H), 3.70 (dd, J=11.2, 2.5, 1H), 3.61 (t, J=11.0, 2H), 3.44 (dd, J=22.6, 9.4, 2H), 3.18-3.04 (m, 2H), 2.90-2.77 (m, 2H), 2.55 (t, J=5.1, 2H), 1.40 (d, J=6.9, 6H), 1.22 (d, J=6.6, 3H), 1.06 (t, J=7.2, 3H). LC/MS-m/z+425.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with sat NaHCO3
  3. extractionextracted three times with 10% MeOH in dichloromethane
  4. dry with materialdried over Magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by HPLC

Sources & evidence

ORD record
ord-7ee46169e7694b2aa1ebd11ed32d382c
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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