Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 70655864, compound

HRID 1409378Notes

Reaction equation

HRID 1409378 reaction equation
[OH:1][C:2]([C:5]1[O:6][CH:7]=[C:8]([C:10]([OH:12])=O)[N:9]=1)([CH3:4])[CH3:3].[NH2:13][C@@H:14]([CH3:31])[CH2:15][N:16]1[CH:20]=[CH:19][C:18]([C:21]2[CH:28]=[C:27]([F:29])[C:24]([C:25]#[N:26])=[C:23]([Cl:30])[CH:22]=2)=[N:17]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[Cl:30][C:23]1[CH:22]=[C:21]([C:18]2[CH:19]=[CH:20][N:16]([CH2:15][C@@H:14]([NH:13][C:10]([C:8]3[N:9]=[C:5]([C:2]([OH:1])([CH3:3])[CH3:4])[O:6][CH:7]=3)=[O:12])[CH3:31])[N:17]=2)[CH:28]=[C:27]([F:29])[C:24]=1[C:25]#[N:26]

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67169360HCID 67169360, compoundHCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile2×

Product 1

HCID 70655864HCID 70655864, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from 2-(2-hydroxypropan-2-yl)oxazole-4-carboxylic acid (2.153 mmol, 0.368 g) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzo-nitrile (2.153 mmol, 0.6 g) and using HBTU (0.215 mmol, 0.082 g) instead of HOBt. DCM (15 ml) was used as the solvent. During the reaction a new batch of starting materials was added to the reaction mixture. The batch contained half the amount of starting materials used in the beginning of the reaction with the exception that (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile was not added at all. The resulting mixture was stirred for 2 days. The mixture was diluted with DCM and washed with Na2CO3 solution and water. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.669 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.13 (d, 3H), 1.52 (s, 6H), 4.27-4.54 (m, 3H), 5.63 (s, 1H), 7.02 (d, 1H), 7.83-7.89 (m, 2H), 7.98 (s, 1H), 8.10 (d, 1H), 8.48 (s, 1H).

Workup

  1. customThe title compound was prepared
  2. customDuring the reaction a new batch of starting materials
  3. additionwas added to the reaction mixture
  4. additionwas not added at all
  5. washwashed with Na2CO3 solution and water
  6. customThe organic phase was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-7209fbf41a7246e2a7d79a8db0a07490
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

Loading…