Diisopropylethylamine → HCID 59451631, compound

HRID 1875033Notes

Reaction equation

HRID 1875033 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][CH2:26][C:27]1[C:28]([F:44])=[C:29]([O:34][C:35]2[CH:36]=[C:37]([CH:40]=[C:41]([Cl:43])[CH:42]=2)[C:38]#[N:39])[C:30]([Cl:33])=[CH:31][CH:32]=1.CC(OC([N:52]1[C:60]2[C:55](=[CH:56][CH:57]=[C:58]([NH:61][S:62]([CH3:65])(=[O:64])=[O:63])[CH:59]=2)[CH:54]=[C:53]1[C:66](O)=[O:67])=O)(C)C.C(N(C(C)C)CC)(C)C>CN(C=O)C>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][NH:25][C:66]([C:53]2[NH:52][C:60]3[C:55]([CH:54]=2)=[CH:56][CH:57]=[C:58]([NH:61][S:62]([CH3:65])(=[O:64])=[O:63])[CH:59]=3)=[O:67])=[C:28]([F:44])[C:29]=1[O:34][C:35]1[CH:36]=[C:37]([C:38]#[N:39])[CH:40]=[C:41]([Cl:43])[CH:42]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 68485386HCID 68485386, compound

Product 1

HCID 59451631HCID 59451631, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (0.083 g, 0.218 mmol) was added to a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.045 g, 0.146 mmol), 1-{[(1,1-dimethylethyl)oxy]carbonyl}-6-[(methylsulfonyl)amino]-1H-indole-2-carboxylic acid (0.037 g, 0.146 mmol) and diisopropylethylamine (0.038 mL, 0.218 mmol) in DMF (1 mL). The mixture was stirred at room temperature overnight. The reaction mixture was extracted with ethyl acetate and water. The organic layer wa sdired over sodium sulfate and concentrated. The residue was triturated with methanol to give the title compound (0.036 g, 45%) as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.56 (s, 1H), 9.53 (br. s., 1H), 8.94 (t, 1H), 7.78 (s, 1H), 7.52 (d, 1H), 7.48 (br. s., 1H), 7.45 (d, 1H), 7.35 (t, 1H), 7.31 (s, 1H), 7.10 (s, 1H), 6.91 (dd, 1H), 4.52 (d, 2 H), 2.87 (s, 3H). ES MS: m/z 547 (M+1).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate and water
  2. concentrationconcentrated
  3. customThe residue was triturated with methanol

Sources & evidence

ORD record
ord-5680480fd96c489d9edf05b46b0f8a09
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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