Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 66576287, compound

HRID 1409361Notes

Reaction equation

HRID 1409361 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([C:15]([OH:17])=O)[N:14]=2)[CH:11]=1)(=[O:4])=[O:3].[NH2:18][C@@H:19]([CH3:36])[CH2:20][N:21]1[CH:25]=[CH:24][C:23]([C:26]2[CH:33]=[C:32]([F:34])[C:29]([C:30]#[N:31])=[C:28]([Cl:35])[CH:27]=2)=[N:22]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[Cl:35][C:28]1[CH:27]=[C:26]([C:23]2[CH:24]=[CH:25][N:21]([CH2:20][C@@H:19]([NH:18][C:15]([C:13]3[N:14]=[C:9]4[CH:8]=[CH:7][C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:11][N:10]4[CH:12]=3)=[O:17])[CH3:36])[N:22]=2)[CH:33]=[C:32]([F:34])[C:29]=1[C:30]#[N:31]

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 70980721HCID 70980721, compound

Product 1

HCID 66576287HCID 66576287, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from 6-(methylsulfonamido)imidazo[1,2-a]pyridine-2-carboxylic acid (0.215 mmol, 0.055 g) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzo-nitrile (0.179 mmol, 0.050 g) using DCM (10 ml) as the solvent. HBTU (0.018 mmol, 6.80 mg) was used instead of HOBt. The mixture was diluted with DCM and washed with Na2CO3 solution and water. The organic phase was evaporated. The water phase and Na2CO3 phase were washed with EtOAc. The evaporated organic phases were combined and purified by preparative HPLC. 0.0174 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.14 (d, 3H), 3.04 (s, 3H), 4.27-4.58 (m, 3H), 7.00 (d, 1H), 7.27 (dd, 1H), 7.57-7.62 (m, 1H), 7.87 (d, 1H), 7.91 (dd, 1H), 7.95-7.97 (m, 1H), 8.36 (d, 1H), 8.49-8.51 (m, 1H), 8.55 (d, 1H), 9.77 (s, 1H).

Workup

  1. customThe title compound was prepared
  2. washwashed with Na2CO3 solution and water
  3. customThe organic phase was evaporated
  4. washThe water phase and Na2CO3 phase were washed with EtOAc
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f6055661d0da49b7a4b3a1ee5632bdfd
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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