Hydrochloric Acid → HCID 58504790, compound

HRID 2367395Notes

Reaction equation

HRID 2367395 reaction equation
[C:1]1([NH:7][C:8](=[O:26])[O:9][CH2:10][C@H:11]2[O:16][CH2:15][C@@H:14]([CH3:17])[N:13]([C:18]3[CH:23]=[C:22](Cl)[N:21]=[C:20]([NH2:25])[N:19]=3)[CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:27]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][C:30]=1[F:38])#[N:28].C([O-])([O-])=O.[K+].[K+].Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.O1CCOCC1>[C:1]1([NH:7][C:8](=[O:26])[O:9][CH2:10][C@H:11]2[O:16][CH2:15][C@@H:14]([CH3:17])[N:13]([C:18]3[CH:23]=[C:22]([C:32]4[CH:33]=[CH:34][C:29]([C:27]#[N:28])=[C:30]([F:38])[CH:31]=4)[N:21]=[C:20]([NH2:25])[N:19]=3)[CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2783130(4-Cyano-3-fluorophenyl)boronic acidHCID 58504371HCID 58504371, compound

Product 1

HCID 58504790HCID 58504790, compoundYield 100.2%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A biphasic suspension of [(2S,5R)-4-(2-amino-6-chloro-4-pyrimidinyl)-5-methyl-2-morpholinyl]methyl phenylcarbamate (123 mg, 0.326 mmol), (4-cyano-3-fluorophenyl)boronic acid (107 mg, 0.651 mmol), PdCl2(dppf).CH2Cl2 adduct (13.3 mg, 0.016 mmol), 2N aqueous K2CO3 (0.488 mL, 0.977 mmol), and 1,4-dioxane (3 mL) was heated in a microwave reactor for 10 minutes at 140° C. The reaction was poured into 0.1 N HCl (30 mL) and CH2Cl2 (50 mL) and the aqueous was extracted with CH2Cl2 (2×50 mL). The combined organics were dried over Na2SO4, and concentrated to yield the title compound (151 mg) as a dark brown oil. LC-MS (ES) m/z=463 [M+H]+.

Workup

  1. extractionthe aqueous was extracted with CH2Cl2 (2×50 mL)
  2. dry with materialThe combined organics were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cc788d81d8f94db5af518997a4061f7c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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