4-Methylmorpholine → 2-Chloro-N-[2-(4-methoxy-phenylamino)-pyrimidin-5-yl]-5-(3-trifluoromethyl-benzoylamino)-benzamide

HRID 1662859Notes

Reaction equation

HRID 1662859 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.[CH3:42][O:43][C:44]1[CH:49]=[CH:48][C:47]([NH:50][C:51]2[N:56]=[CH:55][C:54]([NH2:57])=[CH:53][N:52]=2)=[CH:46][CH:45]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=2)=[CH:7][C:3]=1[C:4]([NH:57][C:54]1[CH:53]=[N:52][C:51]([NH:50][C:47]2[CH:46]=[CH:45][C:44]([O:43][CH3:42])=[CH:49][CH:48]=2)=[N:56][CH:55]=1)=[O:6]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 534011722-Chloro-5-(3-(trifluoromethyl)benzamido)benzoic acidHCID 59652746N2-(4-Methoxyphenyl)pyrimidine-2,5-diamine

Product 1

HCID 249629092-Chloro-N-[2-(4-methoxy-phenylamino)-pyrimidin-5-yl]-5-(3-trifluoromethyl-benzoylamino)-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-5-(3-trifluoromethyl-benzoylamino)-benzoic acid (0.524 g, 1.53 mmol, 1.1 equiv) was combined with 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) (0.305 g, 1.74 mmol, 1.25 equiv) and diluted with DCM (10 mL). This was immediately treated with 4-methyl morpholine (0.458 mL, 4.16 mmol, 3 equiv) and allowed to stir at ambient temperature for 1 hour. Intermediate 68 (0.3 g, 1.38 mmol, 1 equiv) was then added in one portion. Stirring was continued overnight. After 18 h, reaction solvents were removed and resulting crude solids were purified via silica gel chromatography. Eluting with 1:1 EtOAc in Hexanes afforded desired product. Beige solids (0.19 g, 26%).

Workup

  1. stirringStirring
  2. waitwas continued overnight
  3. waitAfter 18 h
  4. customreaction solvents
  5. customwere removed
  6. customresulting crude solids
  7. customwere purified via silica gel chromatography
  8. washEluting with 1:1 EtOAc in Hexanes

Sources & evidence

ORD record
ord-1d4167b8a61b43ebb4462e4214b49b8b
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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