Ammonium Chloride → HCID 178451066, compound

HRID 1500494Notes

Reaction equation

HRID 1500494 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]([C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])=[O:10])=[CH:4][N:3]=1.[C:21]([O:25][C:26](=[O:32])[CH2:27][CH2:28][C:29](O)=[O:30])([CH3:24])([CH3:23])[CH3:22].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[Cl-].[NH4+]>CN(C)C=O>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[CH2:12][NH:11][C:9]([C:5]1[C:6]([OH:8])=[N:7][C:2]([NH:1][C:29](=[O:30])[CH2:28][CH2:27][C:26]([O:25][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:32])=[N:3][CH:4]=1)=[O:10]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 41391074-(Tert-butoxy)-4-oxobutanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178508416HCID 178508416, compound

Product 1

HCID 178451066HCID 178451066, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-amino-N-[(2,4-dichlorophenyl)methyl]-4-hydroxypyrimidine-5-carboxamide (317 mg), 4-tert-butoxy-4-oxobutanoic acid (529 mg), and N,N-diisopropylethylamine (1.06 mL) in N,N-dimethylformamide (8 mL), 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1160 mg) was added at room temperature, and the mixture was stirred at 80° C. for 5 hours. The reaction solution was cooled to room temperature. Then, a saturated aqueous ammonium chloride solution was added thereto, and the mixture was stirred for 10 minutes. The resulting suspension was filtered. The product collected by filtration was washed with water and dried under reduced pressure to obtain the title compound (430 mg).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. stirringthe mixture was stirred for 10 minutes
  3. filtrationThe resulting suspension was filtered
  4. filtrationThe product collected by filtration
  5. washwas washed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-894b6e1d19634f15b9dcff12faa30329
Source dataset
uspto-grants-2015_12
Patent number
US09206168B2

Reaction notes

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