4-Chlorobenzaldehyde → HCID 16105839, compound

HRID 1726498Notes

Reaction equation

HRID 1726498 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](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([CH2:26][NH2:27])=[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[CH2:7][CH2:8][CH:9]([NH:12][S:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([CH2:26][NH2:27])=[CH:18][CH:17]=2)(=[O:14])=[O:15])[CH2:10][CH2:11]1)=[O:5])[CH3:2].[CH:4]([OH:5])=[O:3].[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][CH:9]([NH:12][S:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([CH2:26][NH:27][CH2:33][C:32]3[CH:35]=[CH:36][C:29]([Cl:28])=[CH:30][CH:31]=3)=[CH:18][CH:17]=2)(=[O:14])=[O:15])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 16105839HCID 16105839, compound

Product 2

HCID 16105839HCID 16105839, compoundHCID 66999061HCID 66999061, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

4-(4-Aminomethyl-naphthalene-1-sulfonylamino)-piperidine-1-carboxylic acid ethyl ester (32) was prepared according to the procedure in Scheme 12. To a 25° C. solution of 4-(4-aminomethyl-naphthalene-1-sulfonylamino)-piperidine-1-carboxylic acid ethyl ester (32) (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 to give a solid. The resultant solid was purified by reverse phase HPLC providing 4-{4-[(4-chloro-benzylamino)-methyl]-naphthalene-1-sulfonylamino }-piperidine-1-carboxylic acid ethyl ester formate salt (G-7). 1H NMR (300 MHz, MeOD) δ 8.76 (m, 1H), 8.38 (s, br, 1H), 8.24 (d, 1H), 8.18 (m, 1H), 7.51 (m, 3H), 7.44 (m, 4H), 4.52 (s, 2H), 4.12 (s, 2H), 4.04 (q, 2H), 3.60 (d, 2H), 3.40 (m, 1H), 2.72 (m, 2H), 1.50 (m, 2H), 1.25 (m, 2H), 1.18 (t, 3H); LC/MS m/z 516 (M+H)+.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customto give a solid
  3. customThe resultant solid was purified by reverse phase

Sources & evidence

ORD record
ord-5bbd24888ef1485b8363851b58c6ceb5
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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