Hydrochloric Acid → HCID 25197062, compound

HRID 2067901Notes

Reaction equation

HRID 2067901 reaction equation
[F:1][CH:2]([F:37])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:18]=[C:19]([CH:34]=[CH:35][CH:36]=3)[O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH:26]([C:29]([O:31]CC)=[O:30])[CH2:25][CH2:24]3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1.C1COCC1.[OH-].[Li+].Cl>CO>[F:37][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:18]=[C:19]([CH:34]=[CH:35][CH:36]=3)[O:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][CH:26]([C:29]([OH:31])=[O:30])[CH2:27][CH2:28]3)=[N:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68728956HCID 68728956, compound

Product 1

HCID 25197062HCID 25197062, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To ethyl 1-(2-(3-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenoxy)ethyl)piperidine-4-carboxylate 41 (78 umol) is added THF (3 mL), MeOH (2 mL) and 3M lithium hydroxide (0.5 mmol). The reaction mixture is stirred at rt for 6 h until complete as detected by LCMS. Subsequently the organic solvents are evaporated and the reaction mixture is diluted with water (5 mL) and neutralized with 3M HCl (0.5 mmol). The resulting precipitate is filtered, washed with water and air dried to yield 1-(2-(3-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenoxy)ethyl)piperidine-4-carboxylic acid E1 as white solid. 1H NMR (400 MHz, d6-DMSO) δ 12.12 (s, 1H), 9.79 (s, 1H), 8.85 (s, 2H), 7.78 (d, J=8.0 Hz, 2H), 7.52 (bs, 1H), 7.34 (bd, J=8.0 Hz, 1H), 7.31 (t, J=74.0 Hz, 1H), 7.28 (d, J=8.0 Hz, 1H), 7.18 (t, J=8.0 Hz, 1H), 6.56 (bd, J=8.0 Hz, 1H) 4.05 (m, 2H), 2.88 (m, 2H), 2.67 (m, 2H), 2.20 (m, 1H), 2.09 (m, 2H), 1.78 (m, 2H), 1.57 (m, 2H). MS (m/z) (M+1)+: 484.2.

Workup

  1. customSubsequently the organic solvents are evaporated
  2. additionthe reaction mixture is diluted with water (5 mL)
  3. filtrationThe resulting precipitate is filtered
  4. washwashed with water and air
  5. customdried

Sources & evidence

ORD record
ord-d6927413a7eb413e8ada2454141483a3
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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