Diethyl Ether → HCID 178469801, compound

HRID 963438Notes

Reaction equation

HRID 963438 reaction equation
C(OC([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]#[C:26][C:27]4[CH:32]=[C:31]([CH2:33][C:34]5[C:35]([NH2:41])=[N:36][C:37]([NH2:40])=[N:38][CH:39]=5)[CH:30]=[C:29]([O:42][CH3:43])[C:28]=4[O:44][CH3:45])[CH:23]=3)[C:18](=[O:46])[C:17]([C:47]([O:49][CH2:50][CH3:51])=[O:48])=[CH:16]2)[CH2:11][CH2:10]1)=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OCC)C>C(Cl)Cl>[NH2:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([N:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]#[C:26][C:27]4[CH:32]=[C:31]([CH2:33][C:34]5[C:35]([NH2:41])=[N:36][C:37]([NH2:40])=[N:38][CH:39]=5)[CH:30]=[C:29]([O:42][CH3:43])[C:28]=4[O:44][CH3:45])[CH:23]=3)[C:18](=[O:46])[C:17]([C:47]([O:49][CH2:50][CH3:51])=[O:48])=[CH:16]2)[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 178469802HCID 178469802, compound

Product 1

HCID 178469801HCID 178469801, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

16ad) A suspension of 0.415 g of ethyl 1-(trans-4-tert-butoxycarbonylamino-cyclohexyl)-7-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenylethynyl]-4-oxo-1,4-dihydro-quinoline-3-carboxylate (Example 12t)) in 4 ml of methylene chloride and 0.4 ml of anisole is treated at 0° C. under argon with 1.9 ml of trifluoroacetic acid. The reaction mixture is warmed to room temperature and is stirred at room temperature for 4 hrs. After cooling with ice the reaction mixture is treated with 10 ml of diethyl ether. The separated crystals are filtered off under suction, washed with diethyl ether and dried. The crude product is dissolved in 50 ml of water, the resulting suspension is filtered and the filtrate is lyophilized. 0.39 g (92%) of ethyl 1-(trans-4-amino-cyclohexyl)-7-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenylethynyl]-4-oxo-1,4-dihydro-quinoline-3-carboxylate is obtained as a beige amorphous solid. Mass spectrum (FAB): peaks inter alia at 597 (M++H, 100%), 500 (90%), 454 (92%).

Workup

  1. temperatureAfter cooling with ice the reaction mixture
  2. filtrationThe separated crystals are filtered off under suction
  3. washwashed with diethyl ether
  4. customdried
  5. dissolutionThe crude product is dissolved in 50 ml of water
  6. filtrationthe resulting suspension is filtered

Sources & evidence

ORD record
ord-557b5d7a69444eaaa5a6950f24964e33
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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