Ammonia → HCID 136054490, compound

HRID 606432Notes

Reaction equation

HRID 606432 reaction equation
[OH:1][NH:2][CH:3]([CH:35]([CH3:37])[CH3:36])[CH2:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]([C:24]3[NH:33][C:32](=[O:34])[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)=[O:23])[CH:15]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6].C([N:41]([CH2:45]C)C(C)C)(C)C.ClC(Cl)([O:50]C(=O)OC(Cl)(Cl)Cl)Cl.N>C1COCC1>[NH2:41][C:45]([N:2]([OH:1])[CH:3]([CH:35]([CH3:37])[CH3:36])[CH2:4][S:5]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]([C:24]3[NH:33][C:32](=[O:34])[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)=[O:23])[CH:15]=2)=[CH:12][CH:13]=1)(=[O:6])=[O:7])=[O:50]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 136054509HCID 136054509, compound

Product 1

HCID 136054490HCID 136054490, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of N-[(4′-{[2-(hydroxyamino)-3-methylbutyl]sulfonyl}biphenyl-3-yl)methyl]-4-oxo-3,4-dihydroquinazoline-2-carboxamide obtained in Reference Example 107 (0.050 g, 0.096 mmol) and N,N-diisopropylethylamine (0.017 mL, 0.096 mmol) in THF (10 mL) was added dropwise to a suspension of triphosgene (0.0094 g, 0.032 mmol) in THF (2 mL) at 0° C., and the mixture was stirred at room temperature for 2 hr. 28% Aqueous ammonia (0.065 mL, 0.960 mmol) was added thereto, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from EtOH-water to give the title compound as a white powder (0.045 g, 83%).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was crystallized from EtOH-water

Sources & evidence

ORD record
ord-0baa88c4d3ff4677a5f605546d5aa069
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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