4-Chlorobenzaldehyde → Formate

HRID 561341Notes

Reaction equation

HRID 561341 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][S:13]([C:16]2[C:25]3[C:20](=[C:21]([CH2:26][NH2:27])[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][CH:30]=1.C([BH3-])#N.[Na+]>CO>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][S:13]([C:16]2[C:25]3[C:20](=[C:21]([CH2:26][NH:27][CH2:33][C:32]4[CH:35]=[CH:36][C:29]([Cl:28])=[CH:30][CH:31]=4)[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)(=[O:14])=[O:15])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH:4]([O-:5])=[O:3]

Participants

6

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59717979HCID 59717979, compound

Product 2

HCID 283FormateHCID 10346447HCID 10346447, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a 25° C. solution of 4-(5-aminomethyl-naphthalene-1-sulfonylamino)-piperidine-1-carboxylic acid ethyl ester 55 (62 mg, 0.159 mmol) in MeOH (4 mL) was added 4-chloro-benzaldehyde (45 mg, 0.318 mmol) and sodium cyanoborohydride (50 mg, 0.795 mmol). After stirring for 2 h at 25° C., the solution was concentrated in vacuo and the resultant crude material was purified by reverse phase HPLC to provide the title compound (H-45) as its formate salt. 1H NMR (300 MHz, MeOD) δ 8.78 (d, 1H), 8.38 (s, 1H), 8.33 (m, 2H), 7.70 (m, 3H), 7.45 (m, 4H), 4.57 (s, 2H), 4.20 (s, 2H), 4.05 (q, 2H), 3.75 (d, 2H), 3.20 (m, 1H), 2.75 (m, 2H), 1.50 (m, 2H), 1.25 (m, 2H), 1.17 (t, 3H); LC/MS m/z 516 (M+H)+.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customthe resultant crude material was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-66c7b50f9142486aa902b416fc95cdeb
Source dataset
uspto-grants-2011_11
Patent number
US08063222B2

Reaction notes

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