Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 66576522, compound

HRID 1409321Notes

Reaction equation

HRID 1409321 reaction equation
[CH3:1][C:2]1[N:7]2[CH:8]=[C:9]([C:11]([OH:13])=O)[N:10]=[C:6]2[CH:5]=[C:4]([CH3:14])[N:3]=1.[NH2:15][C@@H:16]([CH3:33])[CH2:17][N:18]1[CH:22]=[CH:21][C:20]([C:23]2[CH:30]=[C:29]([F:31])[C:26]([C:27]#[N:28])=[C:25]([Cl:32])[CH:24]=2)=[N:19]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:32][C:25]1[CH:24]=[C:23]([C:20]2[CH:21]=[CH:22][N:18]([CH2:17][C@@H:16]([NH:15][C:11]([C:9]3[N:10]=[C:6]4[CH:5]=[C:4]([CH3:14])[N:3]=[C:2]([CH3:1])[N:7]4[CH:8]=3)=[O:13])[CH3:33])[N:19]=2)[CH:30]=[C:29]([F:31])[C:26]=1[C:27]#[N:28]

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12744612HCID 12744612, compoundHCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

Product 1

HCID 66576522HCID 66576522, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from 5,7-dimethyl-imidazo[1,2-c]pyrimidine-2-carboxylic acid (0.753 mmol, 0.144 g) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluoro-benzonitrile (0.538 mmol, 0.2 g). DMF (6 ml) was used as a solvent and HBTU (0.054 mmol, 0.020 g) was used instead of HOBt. The crude product was purified by trituration from ACN. 0.045 g of the title compound was obtained. 1H-NMR (400 MHz, CDCl3): δ 1.26 (d, 3H), 2.53-2.56 (m, 3H), 2.82 (s, 3H), 4.30 (dd, 1H), 4.48 (dd, 1H), 4.60-4.72 (m, 1H), 6.63 (d, 1H), 7.23-7.26 (m, 1H), 7.52 (d, 1H), 7.75-7.83 (m, 2H), 8.00-8.06 (m, 1H), 8.27 (d, 114).

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified by trituration from ACN

Sources & evidence

ORD record
ord-d0f11304ecfa45518a23bbdc48e15b9e
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

Loading…