Hydrochloric Acid → HCID 178428295, compound

HRID 2207378Notes

Reaction equation

HRID 2207378 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11]3[CH:12]=[C:13]([C:18]4[CH:19]=[CH:20][C:21]([C:24]([C@H:27]5[CH2:32][CH2:31][C@H:30]([C:33]([O:35]CCCC)=[O:34])[CH2:29][CH2:28]5)([OH:26])[CH3:25])=[N:22][CH:23]=4)[CH:14]=[C:15]([CH3:17])[CH:16]=3)[N:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl.CC(O)C>CO.C(Cl)(Cl)Cl.O>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11]3[CH:12]=[C:13]([C:18]4[CH:19]=[CH:20][C:21]([C:24]([C@H:27]5[CH2:32][CH2:31][C@H:30]([C:33]([OH:35])=[O:34])[CH2:29][CH2:28]5)([OH:26])[CH3:25])=[N:22][CH:23]=4)[CH:14]=[C:15]([CH3:17])[CH:16]=3)[N:5]=2)[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 178451145HCID 178451145, compound

Product 1

HCID 178428295HCID 178428295, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of trans-butyl 4-(1-(5-(3-(4-cyclopropylpyrimidin-2-ylamino)-5-methylphenyl)pyridin-2-yl)-1-hydroxyethyl)cyclohexanecarboxylate (61.0 mg, 0.095 mmol) and NaOH (1 M, 0.480 ml, 0.480 mmol) in MeOH (1 mL) was heated to 80° C. for 1 hour. The reaction mixture was cooled to room temperature, acidified with aqueous 1N HCl and diluted with 9:1 CHCl3:IPA. The mixture was then diluted with water and extracted with 9:1 CHCl3:IPA (3×). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford trans-4-(1-(5-(3-(4-cyclopropylpyrimidin-2-ylamino)-5-methylphenyl)pyridin-2-yl)-1-hydroxyethyl)cyclohexanecarboxylic acid. MS ESI calc'd for C28H33N4O3 [M+H]+ 473. found 473. 1H NMR (500 MHz, DMSO-d6) δ 9.57 (s, 1H), 8.75 (s, 1H), 8.49 (br s, 1H), 8.27 (d, J=5.0 Hz, 1H), 8.00 (br s, 1H), 7.97 (s, 1H), 7.66 (s, 1H), 7.19 (s, 1H), 6.82 (d, J=5.0 Hz, 1H), 5.74 (s, 1H), 2.35 (s, 3H), 2.04-1.73 (m, 5H), 1.56 (s, 3H), 1.30-1.22 (m, 5H), 1.05-1.01 (m, 5H).

Workup

  1. extractionextracted with 9:1 CHCl3
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef0d1645ff2d473a88434a66b661020a
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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