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4-Methylmorpholine → 4-(4-{5-[2-Chloro-5-(3-Trifluoromethyl-Benzoylamino)-Benzoylamino]-Pyrimidin-2-ylamino}-Benzenesulfonyl)-Piperidine-1-Carboxylic Acid tert-Butyl Ester

HRID 1662811
Notes
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Reaction equation

HRID 1662811 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]([OH:16])=O)=[O:7].ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.[C:42]([O:46][C:47]([N:49]1[CH2:54][CH2:53][CH:52]([S:55]([C:58]2[CH:63]=[CH:62][C:61]([NH:64][C:65]3[N:70]=[CH:69][C:68]([NH2:71])=[CH:67][N:66]=3)=[CH:60][CH:59]=2)(=[O:57])=[O:56])[CH2:51][CH2:50]1)=[O:48])([CH3:45])([CH3:44])[CH3:43]>C(Cl)Cl>[C:42]([O:46][C:47]([N:49]1[CH2:50][CH2:51][CH:52]([S:55]([C:58]2[CH:59]=[CH:60][C:61]([NH:64][C:65]3[N:70]=[CH:69][C:68]([NH:71][C:14](=[O:16])[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:23])([F:22])[F:1])[CH:4]=5)[CH:10]=[CH:11][C:12]=4[Cl:18])=[CH:67][N:66]=3)=[CH:62][CH:63]=2)(=[O:56])=[O:57])[CH2:53][CH2:54]1)=[O:48])([CH3:45])([CH3:43])[CH3:44]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 534011722-Chloro-5-(3-(trifluoromethyl)benzamido)benzoic acidHCID 587487264-(4-(5-Amino-pyrimidin-2-ylamino)-benzenesulfonyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59652742
4-(4-{5-[2-Chloro-5-(3-Trifluoromethyl-Benzoylamino)-Benzoylamino]-Pyrimidin-2-ylamino}-Benzenesulfonyl)-Piperidine-1-Carboxylic Acid tert-Butyl Ester
Yield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 1 (Example 2) (0.098 g, 0.286 mmol) was combined with 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) (0.060 g, 0.343 mmol) and diluted with DCM (4 mL). This was immediately treated with 4-methyl morpholine (0.063 mL, 0.55 mmol) and allowed to stir at ambient temperature for 1 h. Intermediate 13 (Example 20) (0.130 g, 0.3 mmol) was then added in one portion. Stirring was continued overnight. After 18 h, reaction solvents were removed and resulting crude solids were purified via HPLC to afford the title compound as a white solid (0.056 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 HPLC

Sources & evidence

ORD record
ord-831b323d55be4aacb75490498736b872
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08030487B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes