Tetrahydrofuran → HCID 66578440, compound

HRID 1528984Notes

Reaction equation

HRID 1528984 reaction equation
C([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[NH2:27])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])C.Cl[C:29]1[C:30]2[C:37]([CH3:38])=[CH:36][S:35][C:31]=2[N:32]=[CH:33][N:34]=1.C1COCC1.[OH-].[Na+]>C(O)(C)C.Cl>[CH3:26][C:23]1[C:22]([NH:27][C:29]2[C:30]3[C:37]([CH3:38])=[CH:36][S:35][C:31]=3[N:32]=[CH:33][N:34]=2)=[C:21]([C:18]2[CH:19]=[CH:20][C:15]([C:12]3[CH:13]=[CH:14][C:9]([C:6]4([C:4]([OH:3])=[O:5])[CH2:7][CH2:8]4)=[CH:10][CH:11]=3)=[CH:16][CH:17]=2)[O:25][N:24]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium Hydroxide2×HCID 2902254-Chloro-5-methylthieno[2,3-d]pyrimidineHCID 665771951-[4'-(4-Amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 66578440HCID 66578440, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
75 °C

Procedure

1-[4′-(4-Amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.0583 g, 0.161 mmol) and 4-chloro-5-methyl-thieno[2,3-d]pyrimidine (0.0297 g, 0.161 mmol) were mixed in isopropyl alcohol (1 mL) and 1 drop of conc. HCl was added. The reaction was heated to 75° C. overnight, then THF (5 mL) was added, followed by NaOH (3N aq., 0.30 mL) and the reaction continued heating and stirring for 50 minutes. An additional portion of NaOH (3N aq., 0.10 mL) was added and the reaction was heated for 1 hour, then cooled. The reaction mixture was submitted to standard aqueous workup then purified on silica gel (30-100% EtOAc in hexanes) to yield the title compound.

Workup

  1. temperaturethe reaction continued heating
  2. temperaturethe reaction was heated for 1 hour
  3. temperaturecooled
  4. customthen purified on silica gel (30-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9533c66b95d447d2b08a111ce6334f50
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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