2-Pyridineethanamine → HCID 22046412, compound

HRID 1830736Notes

Reaction equation

HRID 1830736 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH:16][C:17]([NH:19][C:20]2[CH:25]=[N:24][C:23]([CH3:26])=[CH:22][N:21]=2)=[O:18])=[CH:5][C:6]([C:12]([F:15])([F:14])[F:13])=[C:7]([CH:11]=1)[C:8](O)=[O:9].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:51][CH2:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][N:55]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[CH3:1][O:2][C:3]1[C:4]([NH:16][C:17]([NH:19][C:20]2[CH:25]=[N:24][C:23]([CH3:26])=[CH:22][N:21]=2)=[O:18])=[CH:5][C:6]([C:12]([F:15])([F:13])[F:14])=[C:7]([CH:11]=1)[C:8]([NH:51][CH2:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][N:55]=1)=[O:9]

Participants

6

Reactant 4

HCID 759192-PyridineethanamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22046499HCID 22046499, compound

Product 1

HCID 22046412HCID 22046412, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred solution of 5-methoxy-4-[3-(5-methyl-pyrazin-2-yl)-ureido]-2-trifluoromethyl -benzoic acid (37 mg, 0.1 mmol) in 1 mL NMP at room temperature in a capped reaction vial was added HBTU (42 mg, 0.11 mmol) and the suspension stirred for 15 minutes. 2-aminoethylpyridine (13 μL, 0.11 mmol) was added followed by DIEA (35 μL, 0.2 mmol) and the reaction was stirred overnight. NMP was then removed by bulb to bulb transfer under high vacuum at 70° C. and the residue triturated and filtered with EtOAc to give the desired amide as a tan solid (32 mg, 68%). 1H-NMR (400 MHz, d6-DMSO) δ8.90 (br s, 1H), 8.66 (d, 1H, 8.61 (s, 1H), 8.52 (t, 1H), 8.23 (s, 1H), 8.10 (br m, 1H), 7.61 (br d, 1H), 7.57 (br m, 1H), 7.07 (s, 1H), 4.00 (s, 3H), 3.62 (m, 2H), 3.11 (m, 2H), 2.42 (s, 3H) LRMS (esi, positive) m/e 475.1 (M+1)

Workup

  1. stirringthe reaction was stirred overnight
  2. customNMP was then removed by bulb to bulb transfer under high vacuum at 70° C.
  3. customthe residue triturated
  4. filtrationfiltered with EtOAc

Sources & evidence

ORD record
ord-bbd23194102841c183aec6571ad752b5
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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