1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Ammonium Hydroxide

HRID 1630878Notes

Reaction equation

HRID 1630878 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]1[CH:12]=[N:13][CH:14]=[C:15]([CH:19]=1)[C:16](O)=[O:17].C1C=CC2N(O)N=[N:26]C=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.[Cl-].[NH4+]>CN(C=O)C>[NH4+:2].[OH-:17].[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]1[CH:12]=[N:13][CH:14]=[C:15]([CH:19]=1)[C:16]([NH2:26])=[O:17]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 58215566HCID 58215566, compound

Product 2

HCID 14923Ammonium HydroxideYield 0.1%HCID 58215666HCID 58215666, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A flask is charged with 5-(1-methyl-1H-indol-2-yl)-nicotinic acid (0.037 g, 0.146 mmol), HOBT (0.024 g, 0.175 mmol), EDCI (0.034 g, 0.175 mmol), DIPEA (0.076 mL, 0.439 mmol) and DMF (3 mL). Ammonium chloride (0.012 g, 0.219 mmol) is added and the reaction is stirred at room temperature overnight. Purification by reverse phase HPLC with Xbridge Shield RP18 column and a 0.1% aqueous NH4OH in acetonitrile gradient gives 5-(1-methyl-1H-indol-2-yl)-nicotinamide. 1H NMR (400 MHz, MeOD) δ ppm 3.85 (s, 3H), 6.77 (d, J=0.6 Hz, 1H), 7.08-7.19 (m, 1H), 7.29 (ddd, J=8.2, 7.1, 1.1 Hz, 1H), 7.50 (dd, J=8.3, 0.7 Hz, 1H), 7.65 (d, J=8.0 Hz, 1H), 8.49 (t, J=2.1 Hz, 1H), 8.95 (d, J=2.1 Hz, 1H), 9.09 (d, J=2.1 Hz, 1H). HRMS (ESI) m/z 252.1145 [(M+H)+ Calcd for C15H14N3O: 252.1137].

Workup

  1. customPurification by reverse phase HPLC with Xbridge Shield RP18 column

Sources & evidence

ORD record
ord-9f35c68bf1dd419092e7aa8805912af1
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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