Acetic Acid → HCID 11372753, compound

HRID 415702Notes

Reaction equation

HRID 415702 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][NH:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][CH:21]=1)[CH:14]=[CH:13]2.C(O)(=O)C.C([BH3-])#N.[Na+].[OH-].[Na+]>O.CCOCC>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][NH:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([NH2:26])=[O:25])=[CH:27][CH:28]=1)[CH2:14][CH2:13]2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 11211452HCID 11211452, compound

Product 1

HCID 11372753HCID 11372753, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Mix 4-{5-[(2-Thiophen-2-yl-ethylamino)-methyl]-indol-1-ylmethyl}-benzamide (0.20 g, 0.51 mmol) and acetic acid (5 mL) in a flask. Add sodium cyanoborohydride (0.09 g, 1.52 mmol) and stir for 3 hrs. Neutralize reaction with 5M aqueous NaOH (10 mL) and dilute with water (50 mL). Extract with CH2Cl2 (3×50 mL). Purification on silica using 40:1 CH2Cl2/2M NH3 in CH3OH to 20:1 CH2Cl2/2M NH3 in CH3OH gradient eluent yields the product as an oily substance. Trituration with ether gives the product as a white solid (0.14 g, 72%). Mass spectrum (ion spray): m/z=392.2 (M+1); 1H NMR (DMSO-d6) 7.91 (bs, 1H), 7.82 (d, J=8.1 Hz, 2H), 7.38 (d, J=7.9 Hz, 2H), 7.30 (bs, 1H), 7.27 (d, J=4.8 Hz, 1H), 6.99 (s, 1H), 6.92-6.87 (m, 2H), 6.82 (d, J=2.2 Hz, 1H), 6.46 (d, J=7.9 Hz, 1H), 4.25 (s, 2H), 3.54 (s, 2H), 3.21 (t, J=8.1 Hz, 2H), 2.92-2.81 (m, 4H), 2.69 (t, J=7.1 Hz, 2H).

Workup

  1. extractionExtract with CH2Cl2 (3×50 mL)
  2. customPurification on silica using 40:1 CH2Cl2/2M NH3 in CH3OH to 20:1 CH2Cl2/2M NH3 in CH3OH gradient eluent
  3. customyields the product as an oily substance

Sources & evidence

ORD record
ord-1df69e1cb28a4ae3b1e0617e18702fe0
Source dataset
uspto-grants-2012_01
Patent number
US08088800B2

Reaction notes

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