Hydrochloric Acid → HCID 59239423, compound

HRID 1698046Notes

Reaction equation

HRID 1698046 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:11]=[C:12]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[C:13]4[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][C:14]=4[N:15]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl.O1CCOC[CH2:35]1>>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:11]=[C:12]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][C@@H:28]4[CH3:35])[C:13]4[CH2:19][CH2:18][NH:17][CH2:16][C:14]=4[N:15]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67181541HCID 67181541, compound

Product 1

HCID 59239423HCID 59239423, compound

Procedure

Tert-butyl 2-(1H-indol-5-yl)-4-morpholino-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate (0.199 g, 0.000443 mol) and 4.0 M of Hydrogen chloride in 1,4-Dioxane (3.4 mL) were combined and shaken for 2 hours then concentrated, diluted 10% MeOH in dichloromethane and sat NaHCO3, extracted three times with 10% MeOH in dichloromethane, dried over Magnesium sulfate, filtered, concentrated, and vacuum pump dried overnight, and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 11.18 (s, 1H), 8.56 (s, 1H), 8.12 (dd, J=8.6, 1.4, 1H), 7.42 (d, J=8.6, 1H), 7.36 (t, J=2.7, 1H), 6.53 (s, 1H), 4.10 (d, J=6.7, 1H), 3.95-3.78 (m, 3H), 3.74 (dd, J=11.3, 2.8, 1H), 3.68-3.50 (m, 3H), 3.50-3.39 (m, 1H), 3.02-2.90 (m, 1H), 2.87-2.76 (m, 1H), 2.55 (d, J=11.2, 2H), 1.25 (t, J=10.2, 3H). LC/MS-m/z+350.2 (M+H)+

Workup

  1. concentrationthen concentrated
  2. additiondiluted 10% MeOH in dichloromethane
  3. extractionextracted three times with 10% MeOH in dichloromethane
  4. dry with materialdried over Magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customvacuum pump dried overnight
  8. custompurified by HPLC

Sources & evidence

ORD record
ord-870bdc5918b343b880bafe4716566198
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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