Triphosgene → HCID 46191508, compound

HRID 336875Notes

Reaction equation

HRID 336875 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)=[C:16]([C:33]([F:36])([F:35])[F:34])[CH:15]=1)=[CH:10][C:9]([C:37]1[CH:38]=[N:39][C:40]3[C:45]([CH:46]=1)=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:8][CH:7]=2.Cl[C:48](Cl)([O:50]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[O:50]=[C:48]1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:22][CH2:21]3)=[C:16]([C:33]([F:36])([F:35])[F:34])[CH:15]=2)[C:12]2[C:11]3[CH:10]=[C:9]([C:37]4[CH:38]=[N:39][C:40]5[C:45]([CH:46]=4)=[CH:44][CH:43]=[CH:42][CH:41]=5)[CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[CH2:2][O:1]1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 58524960HCID 58524960, compound

Product 1

HCID 46191508HCID 46191508, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-(3′-(hydroxymethyl)-3,6′-biquinolin-4′-ylamino)-2-(trifluoromethyl)phenyl)piperazine-1-carboxylate (35 mg, 0.05 mmol) in dichloromethane (5 mL) at 0° C. was added triphosgene (16 mg, 0.05 mmol), and the resultant solution was allowed to warm up to room temperature. The reaction was allowed to proceed for 4 h before quenching with a satd. aqueous sodium carbonate solution (3 mL). The reaction mixture was extracted with EtOAc (3×10 mL) and dried over Na2SO4. The crude product was taken onto the next step without further purification. LC-MS: (M+1)=656.30

Workup

  1. custombefore quenching with a satd
  2. extractionThe reaction mixture was extracted with EtOAc (3×10 mL)
  3. dry with materialdried over Na2SO4
  4. customThe crude product was taken onto the next step without further purification

Sources & evidence

ORD record
ord-9e37461f26f7403e821eb893e17e45d7
Source dataset
uspto-grants-2014_11
Patent number
US08889706B2

Reaction notes

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