Hydrochloric Acid → HCID 178484643, compound

HRID 2169437Notes

Reaction equation

HRID 2169437 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH3:44])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([N:35]3[C:39]4=[N:40][CH:41]=[CH:42][CH:43]=[C:38]4[CH:37]=[CH:36]3)[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.Cl>O1CCCC1>[OH:8][CH2:9][CH2:10][N:11]([CH3:44])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([N:35]3[C:39]4=[N:40][CH:41]=[CH:42][CH:43]=[C:38]4[CH:37]=[CH:36]3)[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178484774HCID 178484774, compound

Product 1

HCID 178484643HCID 178484643, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-methyl-amide (405) (300 mg, 0.49 mmol) in tetrahydrofuran (10 mL) was added 1N HCl (2.4 mL) and stirring was continued for 1 h at room temperature. After completion of the reaction, the tetrahydrofuran was removed and the reaction mixture was basified with solid NaHCO3 (to pH 8), extracted with ethyl acetate (3×20 mL) and the organic part was dried and concentrated to yield a crude product which was purified by prep TLC (mobile phase ethyl acetate) to get 5-benzyloxy-6-hydroxy-2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-methyl-amide (406) (210 mg, 86%) as a light yellow sticky solid.

Workup

  1. customAfter completion of the reaction
  2. customthe tetrahydrofuran was removed
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. customthe organic part was dried
  5. concentrationconcentrated
  6. customto yield a crude product which
  7. customwas purified by prep TLC (mobile phase ethyl acetate)

Sources & evidence

ORD record
ord-1574fc529e2c43e09ab8a6d8be544af5
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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