Ammonium Chloride → HCID 86686142, compound

HRID 869193Notes

Reaction equation

HRID 869193 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:25][C:26]1([C:30]2[C:35]([F:36])=[CH:34][CH:33]=[CH:32][N:31]=2)[CH2:29][CH2:28][CH2:27]1)[C:9]1[N:14]=[N:13][C:12]([CH:15]2[N:19]=[C:18]([O:20][CH3:21])[CH:17]([C:22](O)=[O:23])[S:16]2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:38](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Cl-].[NH4+]>C(OCC)(=O)C.CN1C(=O)CCC1>[C:22]([CH:17]1[S:16][CH:15]([C:12]2[N:13]=[N:14][C:9]([N:8]([CH2:25][C:26]3([C:30]4[C:35]([F:36])=[CH:34][CH:33]=[CH:32][N:31]=4)[CH2:27][CH2:28][CH2:29]3)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:11]=2)[N:19]=[C:18]1[O:20][CH3:21])(=[O:23])[NH2:38]

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86686143HCID 86686143, compound

Product 1

HCID 86686142HCID 86686142, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a 50 dram vial was added 2-(6-(t-butoxycarbonyl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)amino)pyridazin-3-yl)-4-methoxy-2,5-dihydrothiazole-5-carboxylic acid (175 mg, 0.34 mmol), HATU (194 mg, 0.51 mmol), HOAt (70 mg, 0.51 mmol), DIPEA (296 μL, 1.7 mmol), NMP (2 mL), and ammonium chloride (180 mg, 3.4 mmol). The reaction was stirred overnight at rt. The reaction was then poured into ethyl acetate (50 mL), washed with aqueous sodium bicarbonate, and brine (50 mL). The organic layer was separated, dried over Na2SO4, filtered, concentrated and purified by silica gel column chromatography (EtOAC/hexanes) to afford 120 mg of t-butyl 6-(5-carbamoyl-4-methoxy-2,5-dihydrothiazol-2-yl)pyridazin-3-yl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)carbamate.

Workup

  1. washwashed with aqueous sodium bicarbonate, and brine (50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (EtOAC/hexanes)

Sources & evidence

ORD record
ord-d3395edc71894993b97a447b37589174
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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