Phosgene → HCID 178518859, compound

HRID 1678736Notes

Reaction equation

HRID 1678736 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[N:17][C:18]=3[NH:28][NH2:29])[N:13]=2)=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:37](Cl)(Cl)=[O:38]>C(Cl)Cl.C1(C)C=CC=CC=1>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:18]4=[N:28][N:29]=[C:37]([OH:38])[N:17]4[CH:16]=[CH:15][C:14]=3[N:13]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 594729242-[4-(1,3-dioxolan-2-yl)phenyl]-5-hydrazinyl-3-phenyl-1,6-Naphthyridine

Product 1

HCID 178518859HCID 178518859, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-(4-[1,3]dioxolan-2-yl-phenyl)-3-phenyl-[1,6]naphthyridin-5-yl]-hydrazine (3-4, 5.3 g, 13.8 mmol) in CH2Cl2 (anhydrous, 40 mL) at 0° C. was added triethylamine (9.7 mL, 68.9 mmol) followed by a rapid addition of phosgene in toluene (2M, 7.6 mL). After stirring for 10 min at room temperature, the mixture was concentrated and water (30 mL) was added. The solid was collected and dried with toluene azeotropically to give the title compound which was used for the next step without further purification. LRMS m/z (M+1) Calcd: 411.1. Found 411.2.

Workup

  1. concentrationthe mixture was concentrated
  2. additionwater (30 mL) was added
  3. customThe solid was collected
  4. dry with materialdried with toluene azeotropically

Sources & evidence

ORD record
ord-b4396d5c00314a848e42e033b57b340c
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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