Acetohydrazide → Benzoic acid, 5-chloro-2-methoxy-4-[[4-(methylamino)-5-(trifluoromethyl)-2-pyrimidinyl]amino]-, 2-acetylhydrazide

HRID 1630342Notes

Reaction equation

HRID 1630342 reaction equation
[Cl:1][C:2]1[C:3]([NH:13][C:14]2[N:19]=[C:18]([NH:20][CH3:21])[C:17]([C:22]([F:25])([F:24])[F:23])=[CH:16][N:15]=2)=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:50]([NH:53][NH2:54])(=[O:52])[CH3:51].CCN(C(C)C)C(C)C>ClCCl>[C:50]([NH:53][NH:54][C:7](=[O:8])[C:6]1[CH:10]=[C:2]([Cl:1])[C:3]([NH:13][C:14]2[N:19]=[C:18]([NH:20][CH3:21])[C:17]([C:22]([F:24])([F:23])[F:25])=[CH:16][N:15]=2)=[CH:4][C:5]=1[O:11][CH3:12])(=[O:52])[CH3:51]

Participants

6

Reactant 4

HCID 14039AcetohydrazideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 84819816HCID 84819816, compound

Product 1

HCID 86688210Benzoic acid, 5-chloro-2-methoxy-4-[[4-(methylamino)-5-(trifluoromethyl)-2-pyrimidinyl]amino]-, 2-acetylhydrazideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 5-chloro-2-methoxy-4-(4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)benzoic acid (144 mg, 50% pure material, 0.19 mmol), HATU (85 mg, 0.22 mmol), acetic hydrazide (16 mg, 0.22 mmol) and DIPEA (81 uL, 0.46 mmol) in dichloromethane (4 mL) was stirred at room temperature for 18 h. The mixture was diluted with dichloromethane (10 mL) and washed with saturated aqueous NaHCO3 solution (10 mL). A solid persisted in the aqueous layer; this was filtered, washed with water and then suspended in methanol. The solid was collected by filtration and dried in a vacuum oven to afford N′-acetoyl-5-chloro-2-methoxy-4-(4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)benzohydrazide as a white solid (68 mg, 85%). This was taken through to the next step without further purification.

Workup

  1. washwashed with saturated aqueous NaHCO3 solution (10 mL)
  2. filtrationthis was filtered
  3. washwashed with water
  4. filtrationThe solid was collected by filtration
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-4f2a8677661f40f8864feef8ddb79bb2
Source dataset
uspto-grants-2014_07
Patent number
US08791130B2

Reaction notes

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