Hydrochloric Acid → HCID 46893390, compound

HRID 1801958Notes

Reaction equation

HRID 1801958 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[N:20]=[C:19]([NH:21][C:22]3[CH:26]=[C:25]([CH3:27])[NH:24][N:23]=3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+].Cl>CO.C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:9]([C:11]2[N:20]=[C:19]([NH:21][C:22]3[CH:26]=[C:25]([CH3:27])[NH:24][N:23]=3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[OH:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 66613908HCID 66613908, compound

Product 1

HCID 46893390HCID 46893390, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To crude (3,4-difluorophenyl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone (553 mg, 1.5 mmol) in 1:1 MeOH/THF (40 mL) at 0° C. was added sodium borohydride (0.09 g, 2.4 mmol), and the solution was stirred for 30 min, after which 6N HCl was added. The mixture was concentrated to dryness, and ca. ⅔ of the residue was purified by silica gel chromatography eluting with 0-15% MeOH/DCM to afford (3,4-difluorophenyl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanol (34 mg). 1H NMR (300 MHz, DMSO-d6) δ 2.26 (s, 3H) 6.03 (s, 1H) 6.22 (s, 1H) 7.45-7.55 (m, 2H) 7.66 (t, 1H) 7.78 (t, 1H) 8.07 (t, 1H) 8.19 (t, 1H) 8.82 (d, 1H) 12.09 (bs, 1H) 12.67 (bs, 1H); LC-MS (ESI) m/z 368 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customca. ⅔ of the residue was purified by silica gel chromatography
  3. washeluting with 0-15% MeOH/DCM

Sources & evidence

ORD record
ord-6420a21c02ed4c2da7e66617b38f9c8a
Source dataset
uspto-grants-2013_01
Patent number
US08349851B2

Reaction notes

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