4-Methylmorpholine → 5-{5-[2-Chloro-5-(3-Trifluoromethyl-Benzoylamino)-Benzoylamino]-Pyrimidin-2-ylamino}-Pyridine-2-Carboxylic Acid (2-Pyrrolidin-1-yl-Ethyl)-Amide

HRID 1662822Notes

Reaction equation

HRID 1662822 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:18])=[C:13]([CH:17]=1)[C:14](O)=[O:15])=[O:7].ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.[N:42]1([CH2:47][CH2:48][NH:49][C:50]([C:52]2[CH:57]=[CH:56][C:55]([NH:58][C:59]3[N:64]=[CH:63][C:62]([NH2:65])=[CH:61][N:60]=3)=[CH:54][N:53]=2)=[O:51])[CH2:46][CH2:45][CH2:44][CH2:43]1>C(Cl)Cl>[N:42]1([CH2:47][CH2:48][NH:49][C:50]([C:52]2[CH:57]=[CH:56][C:55]([NH:58][C:59]3[N:60]=[CH:61][C:62]([NH:65][C:14](=[O:15])[C:13]4[CH:17]=[C:9]([NH:8][C:6](=[O:7])[C:5]5[CH:19]=[CH:20][CH:21]=[C:3]([C:2]([F:22])([F:23])[F:1])[CH:4]=5)[CH:10]=[CH:11][C:12]=4[Cl:18])=[CH:63][N:64]=3)=[CH:54][N:53]=2)=[O:51])[CH2:46][CH2:45][CH2:44][CH2:43]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 534011722-Chloro-5-(3-(trifluoromethyl)benzamido)benzoic acidHCID 587487255-(5-Amino-pyrimidin-2-ylamino)-pyridine-2-carboxylic acid (2-Pyrrolidin-1-yl-ethyl)-amide

Product 1

HCID 249614625-{5-[2-Chloro-5-(3-Trifluoromethyl-Benzoylamino)-Benzoylamino]-Pyrimidin-2-ylamino}-Pyridine-2-Carboxylic Acid (2-Pyrrolidin-1-yl-Ethyl)-AmideYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 1 (Example 2) (0.076 g, 0.222 mmol) was combined with 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) (0.047 g, 0.266 mmol) and diluted with DCM (4 mL). This was immediately treated with 4-methyl morpholine (0.05 mL, 0.443 mmol) and allowed to stir at ambient temperature for 1 h. Intermediate 23 (Example 31) (0.076 g, 0.233 mmol) was then added in one portion. Stirring was continued overnight. After 18 h, reaction solvents were removed and resulting crude solids purified via HPLC to afford the title compound as a white solid (0.081 g, 56%).

Workup

  1. stirringStirring
  2. waitwas continued overnight
  3. waitAfter 18 h
  4. customreaction solvents
  5. customwere removed
  6. customresulting crude solids
  7. custompurified via HPLC

Sources & evidence

ORD record
ord-6c3affb647024bb9ae7d257212a6cb8d
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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