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

HRID 1662823Notes

Reaction equation

HRID 1662823 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=O.ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.[C:37]([O:41][C:42]([N:44]1[CH2:49][CH2:48][CH:47]([S:50]([C:53]2[CH:58]=[CH:57][C:56]([NH:59][C:60]3[N:65]=[CH:64][C:63]([NH2:66])=[CH:62][N:61]=3)=[CH:55][CH:54]=2)(=[O:52])=[O:51])[CH2:46][CH2:45]1)=[O:43])([CH3:40])([CH3:39])[CH3:38]>C(Cl)Cl>[C:37]([O:41][C:42]([N:44]1[CH2:45][CH2:46][CH:47]([S:50]([C:53]2[CH:54]=[CH:55][C:56]([NH:59][C:60]3[N:65]=[CH:64][C:63]([NH:66][C:4](=[O:6])[C:3]4[CH:7]=[C:8]([NH:11][C:12]([C:14]5[S:15][CH:16]=[CH:17][CH:18]=5)=[O:13])[CH:9]=[CH:10][C:2]=4[Cl:1])=[CH:62][N:61]=3)=[CH:57][CH:58]=2)(=[O:51])=[O:52])[CH2:48][CH2:49]1)=[O:43])([CH3:40])([CH3:38])[CH3:39]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 242143502-Chloro-5-[(thiophene-2-carbonyl)amino]-benzoic acidHCID 587487264-(4-(5-Amino-pyrimidin-2-ylamino)-benzenesulfonyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 596527044-[4-(5-{2-Chloro-5-[(Thiophene-2-Carbonyl)-Amino]-Benzoylamino}-Pyrimidin-2-ylamino)-Benzenesulfonyl]-Piperidine-1-Carboxylic Acid tert-Butyl EsterYield 32.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 15 (Example 23) (0.124 g, 0.439 mmol) was combined with 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) (0.093 g, 0.53 mmol) and diluted with DCM (4 mL). This was immediately treated with 4-methyl morpholine (0.10 mL, 0.88 mmol) and allowed to stir at ambient temperature for 1 h. Intermediate 13 (Example 20) (0.20 g, 0.462 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 (0.1 g, 32%).

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-d039f6464deb484887092357544bc076
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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