Lithium Hydroxide → HCID 71511506, compound

HRID 2171937Notes

Reaction equation

HRID 2171937 reaction equation
[F:1][C:2]1[C:3]([NH:28][CH:29]([C:36]2([C:41]([F:44])([F:43])[F:42])[CH2:40][CH2:39][CH2:38][CH2:37]2)[CH2:30][C:31]([O:33]CC)=[O:32])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[N:10](S(C3C=CC(C)=CC=3)(=O)=O)[CH:9]=2)=[N:6][CH:7]=1.[OH-].[Li+]>C1COCC1>[F:1][C:2]1[C:3]([NH:28][CH:29]([C:36]2([C:41]([F:43])([F:44])[F:42])[CH2:40][CH2:39][CH2:38][CH2:37]2)[CH2:30][C:31]([OH:33])=[O:32])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[NH:10][CH:9]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86714788HCID 86714788, compound2×

Product 1

HCID 71511506HCID 71511506, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of racemic ethyl 3-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-ylamino)-3-(1-(trifluoromethyl)cyclopentyl)propanoate, 197a, (0.080 g, 0.120 mmol) in THF (10 mL) was added lithium hydroxide (2 mL of 2N solution). The reaction was refluxed for 3 hours and cooled to room temperature. The non aqueous solvent was removed under reduced pressure and the aqueous layer was adjusted to pH 4. The aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic phases concentrated in vacuo to afford 16 mg of the desired product as a pale yellow solid: 1H NMR (300 MHz, d6-DMSO) δ 8.51 (s, H), 8.25-7.97 (m, 2H), 7.58-7.42 (m, 2H), 7.12 (d, J=7.5 Hz, H), 4.35 (m, H), 2.85 (m, 2H) and 1.27-0.70 (m, 8H) ppm; LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, Retention Time=2.55 minutes (M+H) 456.45.

Workup

  1. temperatureThe reaction was refluxed for 3 hours
  2. customThe non aqueous solvent was removed under reduced pressure
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
  4. concentrationThe combined organic phases concentrated in vacuo

Sources & evidence

ORD record
ord-a52e3e7d16b0418c85c4b37eb97a8baf
Source dataset
uspto-grants-2015_06
Patent number
US09051319B2

Reaction notes

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