Isopropylamine → HCID 59394608, compound

HRID 45069Notes

Reaction equation

HRID 45069 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[CH:27]=[CH:26][N:25]=[C:24]([CH2:28]OS(C)(=O)=O)[CH:23]=4)=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH:36]([NH2:39])([CH3:38])[CH3:37]>>[F:34][C:2]([F:1])([F:35])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[CH:27]=[CH:26][N:25]=[C:24]([CH2:28][NH:39][CH:36]([CH3:38])[CH3:37])[CH:23]=4)=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 59394190HCID 59394190, compound

Product 1

HCID 59394608HCID 59394608, compound

Procedure

A solution of methanesulfonic acid 4-[1-(3-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]pyridine-2-ylmethyl ester (150 mg, 0.30 mmol) and isopropyl amine (5 mL) is stirred at rt for 2 h. The reaction is concentrated under reduced pressure and the residue separated via semi-prep HPLC (C18; 10-100% I/H2O with 0.1% NH4OH) to give 5-[2-(isopropylamino-methyl)-pyridin-4-yloxy]-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide. MS (ESI) m/z 469.2 (M+1); 1H NMR (400 MHz, MeOD) δ ppm 8.25-8.37 (m, 2 H), 7.97 (s, 1 H), 7.88 (d, J=3.8 Hz, 1 H), 7.80 (d, J=8.1 Hz, 1 H), 7.48 (t, J=8.0 Hz, 1 H), 7.36 (d, J=7.6 Hz, 1 H), 7.30 (d, J=2.3 Hz, 1 H), 7.00 (dd, J=9.0, 2.4 Hz, 1 H), 6.90 (d, J=2.3 Hz, 1 H), 6.81 (dd, J=5.8, 2.3 Hz, 1 H), 6.66 (d, J=3.8 Hz, 1 H), 4.01 (s, 2 H), 3.09-3.18 (m, 1 H), 1.18 (d, J=6.6 Hz, 6 H).

Workup

  1. concentrationThe reaction is concentrated under reduced pressure
  2. customthe residue separated via semi-prep HPLC (C18; 10-100% I/H2O with 0.1% NH4OH)

Sources & evidence

ORD record
ord-3ea61e9bd4184837a6c587ba43b481dc
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Reaction notes

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