Triethylamine → HCID 24826149, compound

HRID 910938Notes

Reaction equation

HRID 910938 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=3[C:17]([OH:19])=O)[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.C(N(CC)CC)C.[Cl:31]C(OCC)=O.[CH:37]([NH:40][CH2:41][CH2:42][NH2:43])([CH3:39])[CH3:38]>C1COCC1>[ClH:31].[ClH:31].[CH:37]([NH:40][CH2:41][CH2:42][NH:43][C:17](=[O:19])[C:16]1[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=1[O:14][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]=2)[CH:13]=1)([CH3:39])[CH3:38]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 88098N-IsopropylethylenediamineHCID 24825978HCID 24825978, compound

Product 1

HCID 24826149HCID 24826149, compoundYield 149.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the method of Example 32, 2-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoic acid (0.100 g, 0.3055 mmol), triethylamine (0.2129 mL, 1.527 mmol), ethyl chloroformate (0.03213 mL, 0.3360 mmol), N-isopropyl-ethylenediamine (0.1143 mL, 0.9164 mmol) in THF (2 mL) were reacted to provide N-(2-(isopropylamino)ethyl)-2-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzamide dihydrochloride (0.122 g, 81.62% yield) as an off white solid. 1H NMR (DMSO) δ 8.63 (bs, 1H), 8.55 (m, 1H), 8.18 (d, 1H), 7.76 (dd, 1H), 7.62 (dt, 1H), 7.42 (dt, 1H), 7.27 (d, 1H), 6.59 (s, 1H), 6.56 (m, 1H), 6.53 (m, 1H), 3.42 (m, 2H), 3.25 (m, 1H), 2.86 (m, 2H), 2.23 (d, 3H), 1.17 (d, 6H); Mass spectrum (esi) m/z=412 (100) (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-182be2aa198f49bc89a32c25ac645fcf
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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