Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 70981105, compound

HRID 1409332Notes

Reaction equation

HRID 1409332 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH:10]=[C:11]([C:13]([OH:15])=O)[N:12]=2)[CH:9]=1)([O-:3])=[O:2].[NH2:16][C@@H:17]([CH3:34])[CH2:18][N:19]1[CH:23]=[CH:22][C:21]([C:24]2[CH:31]=[C:30]([F:32])[C:27]([C:28]#[N:29])=[C:26]([Cl:33])[CH:25]=2)=[N:20]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:33][C:26]1[CH:25]=[C:24]([C:21]2[CH:22]=[CH:23][N:19]([CH2:18][C@@H:17]([NH:16][C:13]([C:11]3[N:12]=[C:7]4[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]4[CH:10]=3)=[O:15])[CH3:34])[N:20]=2)[CH:31]=[C:30]([F:32])[C:27]=1[C:28]#[N:29]

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 33949666-nitroimidazo[1,2-a]pyridine-2-carboxylic acidHCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

Product 1

HCID 70981105HCID 70981105, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from 6-nitroimidazo[1,2-a]pyridine-2-carboxylic acid (0.551 mmol, 0.114 g) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzo-nitrile (0.459 mmol, 0.128 g). DMF (4 ml) was used as the solvent and HBTU (0.046 mmol, 0.017 g) was used instead of HOBt. The crude product was purified by preparative HPLC. 0.0405 g of the title compound was obtained. 1H-NMR (400 MHz, MeOH-d4): δ 1.37 (d, 3H), 4.30-4.37 (m, 1H), 4.38-4.46 (m, 1H), 4.59-4.72 (m, 1H), 6.72 (d, 1H), 7.54 (d, 1H), 7.68 (d, 1H), 7.72 (s, 1H), 7.78 (d, 1H), 8.15-8.21 (m, 1H), 8.38 (s, 1H), 10.40-10.44 (m, 1H).

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-2f4dc99df76c4b0ead174d75f14bcfd6
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

Loading…