Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 66576286, compound

HRID 1409358Notes

Reaction equation

HRID 1409358 reaction equation
[CH3:1][N:2]([CH3:18])[C:3](=[O:17])[NH:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=2)[CH:10]=1.[NH2:19][C@@H:20]([CH3:37])[CH2:21][N:22]1[CH:26]=[CH:25][C:24]([C:27]2[CH:34]=[C:33]([F:35])[C:30]([C:31]#[N:32])=[C:29]([Cl:36])[CH:28]=2)=[N:23]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:36][C:29]1[CH:28]=[C:27]([C:24]2[CH:25]=[CH:26][N:22]([CH2:21][C@@H:20]([NH:19][C:14]([C:12]3[N:13]=[C:8]4[CH:7]=[CH:6][C:5]([NH:4][C:3]([N:2]([CH3:1])[CH3:18])=[O:17])=[CH:10][N:9]4[CH:11]=3)=[O:16])[CH3:37])[N:23]=2)[CH:34]=[C:33]([F:35])[C:30]=1[C:31]#[N:32]

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 70981082HCID 70981082, compound

Product 1

HCID 66576286HCID 66576286, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from 6-(3,3-dimethylureido)imidazo[1,2-a]pyridine-2-carboxylic acid (0.270 mmol, 0.067 g) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (0.108 mmol, 0.04 g) using DMF (4 ml) as the solvent. HBTU (0.027 mmol, 10.24 mg) was used instead of HOBt. The product precipitated into the water phase and was separated by filtration. The organic phase also contained the product. The organic phase was dried, filtered and evaporated. The combined precipitates were purified by preparative HPLC. 0.0192 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.13 (d, 3H), 2.95 (s, 6H), 4.30-4.54 (m, 3H), 7.01 (d, 1H), 7.40-7.45 (m, 1H), 7.47-7.52 (m, 1H), 7.87 (d, 1H), 7.93 (dd, 1H), 7.97 (s, 1H), 8.30 (s, 1H), 8.39 (bs, 1H), 8.49 (d, 1H), 8.87-8.91 (m, 1H).

Workup

  1. customThe title compound was prepared
  2. customThe product precipitated into the water phase
  3. customwas separated by filtration
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe combined precipitates
  8. customwere purified by preparative HPLC

Sources & evidence

ORD record
ord-ec54241cf23c464d8611bff2042c8a06
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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