Ammonia → HCID 71466085, compound

HRID 572667Notes

Reaction equation

HRID 572667 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:15]=[C:14]([CH3:16])[N:13]=[C:12]([C:17]3[CH2:21][CH:20]([C:22]4[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][CH:23]=4)[O:19][N:18]=3)[CH:11]=2)=[O:9])=[CH:4][C:3]=1[O:33][CH3:34].C[N:36](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.N>CN(C=O)C>[C:26]([C:25]1[CH:29]=[CH:30][C:22]([CH:20]2[O:19][N:18]=[C:17]([C:12]3[N:13]=[C:14]([CH3:16])[N:15]=[C:10]([C:8]([NH:7][CH2:6][C:5]4[CH:31]=[CH:32][C:2]([F:1])=[C:3]([O:33][CH3:34])[CH:4]=4)=[O:9])[CH:11]=3)[CH2:21]2)=[CH:23][CH:24]=1)(=[O:28])[NH2:36]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86675922HCID 86675922, compound

Product 1

HCID 71466085HCID 71466085, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-(3-(6-(4-fluoro-3-methoxybenzylcarbamoyl)-2-methylpyrimidin-4-yl)-4,5-dihydroisoxazol-5-yl)benzoic acid (0.1 g, 0.215 mmol) in DMF (10 mL) was added HATU (0.123 g, 0.323 mmol) and DIEA (0.055 g, 0.43 mmol). The reaction mixture was stirred at RT for about 10 min. Ammonia solution (3 mL) was added and the reaction mixture stirred for about another 2 h. The reaction mixture was diluted with ice cold water (20 mL). The solid which was obtained was filtered, washed with water and dried under vacuum to afford 6-(5-(4-carbamoylphenyl)-4,5-dihydroisoxazol-3-yl)-N-(4-fluoro-3-methoxybenzyl)-2-methylpyrimidine-4-carboxamide (0.05 g), (50%) as an off white solid. LC/MS (Table 1, Method c) R1=4.48 min. MS m/z: 464.2 (M+H)+.

Workup

  1. stirringthe reaction mixture stirred for about another 2 h
  2. customThe solid which was obtained
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-beb56e9582094fa89b8bb9e5921fb30b
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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