Ethanolamine → HCID 90467011, compound

HRID 1753251Notes

Reaction equation

HRID 1753251 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:11][C:12]3[C:17]([CH3:18])=[C:16]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])[CH:15]=[CH:14][N:13]=3)[CH:9]=[C:8]([C:25](O)=[O:26])[C:5]2=[N:6][CH:7]=1.CN1C(=O)CCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:59]([CH2:61][NH2:62])[OH:60].C(N(CC)CC)C>>[OH:60][CH2:59][CH2:61][NH:62][C:25]([C:8]1[C:5]2=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=[C:4]2[N:10]([CH2:11][C:12]2[C:17]([CH3:18])=[C:16]([O:19][CH2:20][C:21]([F:22])([F:24])[F:23])[CH:15]=[CH:14][N:13]=2)[CH:9]=1)=[O:26]

Participants

6

Reactant 5

HCID 700EthanolamineHCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117819062HCID 117819062, compound

Product 1

HCID 90467011HCID 90467011, compoundYield 25.4%

Procedure

See FIG. 23(b). 6-methyl-1-((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (55 mg, 0.14 mmol) and NMP (13.95 μl, 0.14 mmol) was taken in a 50 ml single necked flask equipped with an air condenser connected to nitrogen source. HATU (66.2 mg, 0.17 mmol) was added to get a suspension. Added ethanol amine (17.50 μl, 0.29 mmol) followed by the addition of triethyl amine (60.6 μl, 0.43 mmol). The reaction mass was stirred at RT for 5 minutes. LCMS showed completion of the reaction. The crude compound was purified by Gilson Prep HPLC to get pure N-(2-hydroxyethyl)-6-methyl-1-((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (15.00 mg, 24.49%). ES+MS m/z: 423 (M+I). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.23 (s, 3 H ) 2.39 (s, 3 H ) 3.45 (br. s., 2 H ) 3.53 (br. s., 2 H ) 4.83 (s, 1 H ) 4.90 (d, J=9.04 Hz, 2 H ) 5.62 (s, 2 H ) 7.06 (d, J=5.65 Hz, 1 H ) 7.75 (s, 1 H ) 8.07 (s, 1 H ) 8.17 (d, J=5.09 Hz, 1 H ) 8.32 (s, 1H ) 8.79 (s, 1 H ).

Workup

  1. customequipped with an air condenser
  2. customto get a suspension
  3. customcompletion of the reaction
  4. customThe crude compound was purified by Gilson Prep HPLC

Sources & evidence

ORD record
ord-0b2626977b3f41668cdca240f72021f7
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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