Hydrochloric Acid → 4-(5-fluoro-2-methoxyphenyl)-6-(piperidin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 527990Notes

Reaction equation

HRID 527990 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:30][CH3:31])=[C:6]([C:8]2[C:9]3[CH:16]=[C:15]([CH:17]4[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]4)[NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:7]=1.Cl>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:30][CH3:31])=[C:6]([C:8]2[C:9]3[CH:16]=[C:15]([CH:17]4[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]4)[NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90418838tert-butyl 4-(4-(5-fluoro-2-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)piperidine-1-carboxylate

Product 1

HCID 862717544-(5-fluoro-2-methoxyphenyl)-6-(piperidin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 1D (100 mg, 0.23 mmol) in dichloromethane (2 mL), was added hydrogen chloride-saturated ethyl acetate (2 mL) and the mixture was stirred at room temperature for 2 hours. The mixture was concentrated and purified by preparative HPLC (Agilent AD/SP/C18-25/011 reversed phase column) eluting with a gradient of 0.01% trifluoroacetic acid in water to 1:1 methanol/acetonitrile to afford the title compound as the hydrochloride salt. LCMS: 327.1 (M+H)+; 1H NMR (400 MHz, DMSO-d6/D2O): δ 1.77-1.87 (m, 2H), 2.23 (d, J=12 Hz, 2H), 3.0-3.06 (m, 2H), 3.33-3.41 (m, 3H), 3.79 (s, 3H), 6.45 (s, 1H), 7.29-7.32 (m, 1H), 7.44-7.50 (m, 2H), 8.99 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative HPLC (Agilent AD/SP/C18-25/011 reversed phase column)
  3. washeluting with a gradient of 0.01% trifluoroacetic acid in water to 1:1 methanol/acetonitrile

Sources & evidence

ORD record
ord-ba78518e8b2a458c90b88768b9d688dc
Source dataset
uspto-grants-2016_05
Patent number
US09346813B2

Reaction notes

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