2-(Methylamino)ethanol → HCID 59149702, compound

HRID 1675074Notes

Reaction equation

HRID 1675074 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:25][C:26]([F:55])([F:54])[C:27]1[N:31]2[N:32]=[C:33]([N:36]3[CH2:41][CH2:40][CH:39]([C:42]4[C:50]5[C:45](=[CH:46][CH:47]=[C:48]([C:51]([OH:53])=O)[CH:49]=5)[NH:44][CH:43]=4)[CH2:38][CH2:37]3)[CH:34]=[CH:35][C:30]2=[N:29][N:28]=1.[CH3:56][NH:57][CH2:58][CH2:59][OH:60].CCN(C(C)C)C(C)C>CN(C=O)C>[OH:60][CH2:59][CH2:58][N:57]([CH3:56])[C:51]([C:48]1[CH:49]=[C:50]2[C:45](=[CH:46][CH:47]=1)[NH:44][CH:43]=[C:42]2[CH:39]1[CH2:38][CH2:37][N:36]([C:33]2[CH:34]=[CH:35][C:30]3[N:31]([C:27]([C:26]([F:25])([F:54])[F:55])=[N:28][N:29]=3)[N:32]=2)[CH2:41][CH2:40]1)=[O:53]

Participants

6

Reactant 4

HCID 80162-(Methylamino)ethanolHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67339697HCID 67339697, compound

Product 1

HCID 59149702HCID 59149702, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (139 mg, 0.37 mmol) was added portionwise at ambient temperature to a stirred mixture of 3-[1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]-1H-indole-5-carboxylic acid (150 mg, 0.35 mmol), 2-(methylamino)ethanol (0.034 mL, 0.42 mmol) and DIPEA (0.073 mL, 0.42 mmol) in DMF (2.0 mL). The resulting solution was stirred for 2 hours then purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% ammonia) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford N-(2-hydroxyethyl)-N-methyl-3-[1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]-1H-indole-5-carboxamide (155 mg, 91%) as a colourless solid.

Workup

  1. customthen purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length)
  2. additionFractions containing the desired compound
  3. customwere evaporated to dryness

Sources & evidence

ORD record
ord-cbf11edc404842afa25ea32140bfd5dd
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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