Methanol → HCID 59656487, compound

HRID 1726476Notes

Reaction equation

HRID 1726476 reaction equation
N[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][C@H:8]([NH:11][S:12]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([NH:25][C:26](=[O:34])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[CH3:33])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[C@H:7]([CH2:35][CH3:36])[CH2:6]1)=[O:4].[C:37]([BH3-])#[N:38].[Na+].[CH3:41]O>>[CH2:35]([C@H:7]1[C@@H:8]([NH:11][S:12]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([NH:25][C:26](=[O:34])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[CH3:33])=[CH:17][CH:16]=2)(=[O:13])=[O:14])[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][NH:38][CH2:37][CH3:41])[CH2:6]1)[CH3:36]

Participants

4

Reactant 3

HCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 59656514HCID 59656514, compound

Product 1

HCID 59656487HCID 59656487, compound

Conditions

Temperature
25 °C

Procedure

To a 25° C. solution of (±)-(cis)-N-{4-[1-(2-amino-acetyl)-3-ethyl-piperidin-4-ylsulfamoyl]-naphthalen-1-yl}-2-methyl-benzamide (C-131) (65 mg, 0.128 mmol) in MeOH (4 mL) was added acetyl aldehyde (5.62 mg, 0.128 mmol) and sodium cyanoborohydride (40 mg, 0.64 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 to provide the title compound. 1H NMR (300 MHz, MeOD) δ 8.85 (d, 1H), 8.33 (d, 1H), 8.25 (d, 1H), 7.94 (d, 1H), 7.71 (m, 3H), 7.43 (m, 1H), 7.35 (m, 2H), 3.55 (m, 5H), 3.20 (m, 2H), 2.85 (m, 2H), 2.56 (s, 3H), 1.25 (m, 7H), 0.50 (m, 3H); LC/MS m/z 537 (M+H)+

Workup

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

Sources & evidence

ORD record
ord-0d30c9064f2c44139eb5f690555ce893
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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