Nitrogen → [1-(5-Hydroxymethyl-furan-2-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester

HRID 2064913Notes

Reaction equation

HRID 2064913 reaction equation
N#N.C[O:4][C:5]([C:7]1[O:8][C:9]([CH2:12][N:13]2[CH:17]=[C:16]([NH:18][C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])=[O:20])[CH:15]=[N:14]2)=[CH:10][CH:11]=1)=O.[BH4-].[Na+]>CO>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][O:21][C:19](=[O:20])[NH:18][C:16]1[CH:15]=[N:14][N:13]([CH2:12][C:9]2[O:8][C:7]([CH2:5][OH:4])=[CH:11][CH:10]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 33347405-[4-(2-Chloro-benzyloxycarbonylamino)-pyrazol-1-ylmethyl]-furan-2-carboxylic acid methyl esterHCID 4311764Sodium borohydride

Product 1

HCID 66928887[1-(5-Hydroxymethyl-furan-2-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-[4-(2-chloro-benzyloxycarbonylamino)-pyrazol-1-ylmethyl]-furan-2-carboxylic acid methyl ester (3.30 g, 8.46 mmol) in MeOH (33.0 mL) was treated portionwise, at rt with NaBH4 (3.33 g, 84.60 mmol). The reaction mixture was stirred at rt overnight before being quenched by pouring in sat. aq. NH4Cl (100 mL), extracted with EA (3×100 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (30:70 hept-EA) gave the title compound. TLC: rf (30:70 hept-EA)=0.22. LC-MS-conditions 02: tR=0.86 min; [M+H]+=362.32. 1H NMR (400 MHz, CDCl3) δ 2.94 (s, 1H), 4.52 (s, 2H), 5.15 (s, 2H), 5.28 (s, 2H), 6.21 (s, 1H), 6.28 (s, 1H), 7.04 (s, 1H), 7.22-7.35 (m, 2H), 7.35 (s, 1H), 7.35-7.46 (m, 2H), 7.69 (s, 1H).

Workup

  1. custombefore being quenched
  2. additionby pouring in sat. aq. NH4Cl (100 mL)
  3. extractionextracted with EA (3×100 mL)
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (30:70 hept-EA)

Sources & evidence

ORD record
ord-ab83fba18fc64b72b1e12192f452bde3
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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