Dimethylamine → HCID 66712251, compound

HRID 1262386Notes

Reaction equation

HRID 1262386 reaction equation
[CH3:1][S:2]([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=3[O:15][CH2:16][C:17](O)=[O:18])[N:6]2[N:5]=1)=[O:3].[CH3:24][NH:25][CH3:26].O1CCCC1.CN1CCOCC1.CN(C)C=O>>[CH3:1][S:2]([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=3[O:15][CH2:16][C:17]([N:25]([CH3:26])[CH3:24])=[O:18])[N:6]2[N:5]=1)=[O:3]

Participants

6

Reactant 5

HCID 674DimethylamineHCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 66712594HCID 66712594, compound

Product 1

HCID 66712251HCID 66712251, compoundYield 76%

Procedure

[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenoxy]-acetic acid (197 mg, 0.000594 mol), 2.0 M of Dimethylamine in Tetrahydrofuran (0.400 mL, 0.000800 mol) N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.147 g, 0.000767 mol) 1-Hydroxybenzotriazole (0.109 g, 0.000807 mol), 4-Methylmorpholine (0.0850 mL, 0.000773 mol) and N,N-Dimethylformamide (4.9 mL, 0.063 mol) were combined and stirred for 2.5 hours. The reaction was concentrated and purified by normal phase silica gel chromatography eluting with dichloromethane /methanol/ammonium hydroxide to yield a brown solid, 2-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenoxy]-N,N-dimethyl-acetamide (162 mg, 76%). LCMS: m/z=359.13 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ 9.29 (s, 1H), 7.89 (d, 1H, J=7.6 Hz), 7.62 (d, 1H, J=4.7 Hz), 7.44 (m, 1H), 7.30 (d, 1H, J=4.7 Hz), 7.18 (d, 1H, J=8.4 Hz), 7.13 (m, 1H), 4.94 (s, 2H), 2.94 (s, 3H), 2.92 (s, 3H), 2.82 (s, 3H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by normal phase silica gel chromatography
  3. washeluting with dichloromethane /methanol/ammonium hydroxide

Sources & evidence

ORD record
ord-72a8ffdf7c4f4ae1ba1cfb673b2d9fc1
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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