Hydrochloric Acid → HCID 59239640, compound

HRID 1697977Notes

Reaction equation

HRID 1697977 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[N:17]=[C:18]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][C@@H:34]4[CH3:39])[C:19]4[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][C:20]=4[N:21]=3)=[CH:12][CH:11]=2)[NH:4][C:3]1=[O:40].Cl>O1CCOCC1>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[N:17]=[C:18]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][C@@H:34]4[CH3:39])[C:19]4[CH2:25][CH2:24][NH:23][CH2:22][C:20]=4[N:21]=3)=[CH:12][CH:11]=2)[NH:4][C:3]1=[O:40]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67180068HCID 67180068, compound

Product 1

HCID 59239640HCID 59239640, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Step 2—Synthesis of compound um: (S)-Tert-butyl 2-(4-(1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-ylamino)phenyl)-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate (0.196 g, 0.000357 mol) and 4.0 M of Hydrogen chloride in 1,4-Dioxane (5.00 mL) were mixed and stirred for 2 hours. The mixture was concentrated, diluted with sat NaHCO3 and extracted three times with 10% MeOH in dichloromethane. The aqueous layer was lyophilized, slurried in MeOH, vacuum filtered, and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.95 (s, 1H), 8.28 (d, J=8.7, 2H), 8.23 (s, 1H), 7.28 (d, J=8.7, 2H), 6.52 (s, 1H), 5.02 (s, 1H), 4.11 (d, J=6.4, 1H), 3.88 (d, J=11.1, 3H), 3.71 (dd, J=11.3, 2.8, 1H), 3.65-3.56 (m, 3H), 3.08 (s, 3H), 2.99-2.92 (m, 1H), 2.87-2.80 (m, 1H), 2.58 (s, 2H), 1.24 (d, J=6.6, 3H). LC/MS-m/z+450.2 (M+H)+

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with sat NaHCO3
  3. extractionextracted three times with 10% MeOH in dichloromethane
  4. filtrationvacuum filtered
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-2b23185146524337b0b2cf9048f634b8
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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