Diisopropylethylamine → HCID 21081769, compound

HRID 2117160Notes

Reaction equation

HRID 2117160 reaction equation
Cl.Cl.[F:3][C:4]1[CH:5]=[C:6]([NH:31]C(NC(=O)CC2C=CC(F)=CC=2)=S)[CH:7]=[CH:8][C:9]=1[O:10][C:11]1[C:16]2=[C:17]([CH3:30])C(OCCN3CCN(C)CC3)=CN2N=CN=1.[OH:45][C:46]1[N:54]=[CH:53][CH:52]=[CH:51][C:47]=1[C:48]([OH:50])=O.CN(C(O[N:63]1N=NC2C=[CH:67][CH:68]=[N:69][C:64]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[NH:63]1[C:64]2=[N:69][CH:68]=[CH:67][C:11]([O:10][C:9]3[CH:8]=[CH:7][C:6]([NH:31][C:48]([C:47]4[C:46](=[O:45])[NH:54][CH:53]=[CH:52][CH:51]=4)=[O:50])=[CH:5][C:4]=3[F:3])=[C:16]2[CH:17]=[CH:30]1

Participants

7

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 1317262361-(3-Fluoro-4-(5-methyl-6-(2-(4-methylpiperazin-1-yl)ethoxy)pyrrolo[2,1-f][1,2,4] triazin-4-yloxy)phenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea, bis-hydrochloride salt2×HCID 178418543HCID 178418543, compound

Product 1

HCID 21081769HCID 21081769, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorobenzenamine (24 mg, 0.1 mmol, Compound B of Example 132), 2-hydroxynicotinic acid (27 mg, 0.2 mmol), and HATU (76 mg, 0.2 mmol) in DMF (1 mL) was added DIPEA (0.1 mL) and DMAP (5 mg). The resulting mixture was stirred at rt for 2 h and concentrated in vacuo. The residue was was purified by preparative HPLC to give the desired product (8 mg, 22%) as a white solid. LC/MS(ESI+) m/z 365 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was was purified by preparative HPLC

Sources & evidence

ORD record
ord-afcff95c8ee54c33a51efffd2e573800
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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