Hydrochloric Acid → HCID 21073794, compound

HRID 1373657Notes

Reaction equation

HRID 1373657 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]3[CH:23]=[CH:24][C:25]4[CH:30]=[N:29][C:28](=[O:31])[NH:27][C:26]=4[N:32]=3)[CH2:13][CH2:12]2)[CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].Cl.CCOCC>C1COCC1.CO>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]3[CH:23]=[CH:24][C:25]4[CH2:30][NH:29][C:28](=[O:31])[NH:27][C:26]=4[N:32]=3)[CH2:15][CH2:16]2)[CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 21073791HCID 21073791, compound

Product 1

HCID 21073794HCID 21073794, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 7-[4-(4-chroman-8-yl-piperazin-1-yl)-butoxy]-1H-pyrido[2,3-d]pyrimidin-2-one (320 mg) in THF (6 mL) and MeOH (2 mL) was added NaBH4 (54 mg) in portions. After the addition was over, the mixture was kept stirring overnight. The reaction was quenched with H2O. The mixture was extracted with CH2Cl2 (3×50 mL). The combined organic phases were dried over Na2SO4 and concentrated. The residue was purified by chromatography on silica gel to give a semi-solid which was converted to its HCl salt by treating with 1 equivalent of 1 N HCl in a mixed solvent of THF and Et2O to give the title compound (147 mg) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.20 (s, 1H), 7.40 (d, 1H), 6.98 (s, 1H), 7.70 (m, 3H), 6.25 (d, 1H), 4.30–4.06 (m, 6H), 3.60–3.30 (m, 4H), 3.15 (m, 4H), 3.00–2.70 (, 4H), 2.00–1.60 (m, 6H).

Workup

  1. additionAfter the addition
  2. customThe reaction was quenched with H2O
  3. extractionThe mixture was extracted with CH2Cl2 (3×50 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel
  7. customto give a semi-solid which

Sources & evidence

ORD record
ord-304444adade74457a572ba1024204ae5
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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