Diisopropylethylamine → HCID 66957497, compound

HRID 570490Notes

Reaction equation

HRID 570490 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([NH:10][C:11]3[CH:15]=[CH:14][S:13][C:12]=3[C:16](Cl)=[O:17])=[C:4]2[CH:3]=[CH:2]1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]([NH2:32])[CH2:28][N:29]([CH3:31])[CH3:30].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:31][N:29]([CH3:30])[CH2:28][CH:27]([NH:32][C:16]([C:12]1[S:13][CH:14]=[CH:15][C:11]=1[NH:10][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:1][CH:2]=[CH:3][C:4]=12)=[O:17])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[O:20][CH3:19]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 16793344HCID 16793344, compoundHCID 77231083HCID 77231083, compound

Product 1

HCID 66957497HCID 66957497, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 40-mL vial with magnetic stir bar at 25° C. under a nitrogen atmosphere was added 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl chloride (0.26 g, 0.94 mmol) and anhydrous DCM (8 mL). 1-(2-Methoxy-phenyl)-N*2*,N*2*-dimethyl-ethane-1,2-diamine (0.2 g, 1.0 mmol) was then added followed by the diisopropylethylamine (0.6 g, 0.8 mL, 4.7 mmol) and stirring continued×16 hours. The solvent was evaporated under a nitrogen stream and the resulting residue purified via preparative HPLC (0.1% triethylamine/1% acetonitrile mixture in water and methanol) afforded the desired product as a white solid (59.1 mg, 14% yield). LCMS m/e 436 (M+H). 1H NMR (400 MHz, DMSO-d6) ppm 2.12 (s, 6H) 2.25 (dd, J=12.38, 4.27 Hz, 1H) 2.60 (dd, J=12.34, 9.78 Hz, 1H) 3.77 (s, 3H) 5.44-5.52 (m, 1H) 6.41 (dd, J=3.36, 1.18 Hz, 1H) 6.66 (d, J=5.44 Hz, 1H) 6.84 (td, J=7.42, 0.71 Hz, 1H) 6.92-6.97 (m, 1H) 7.16-7.22 (m, 1H) 7.24 (dd, J=7.57, 1.56 Hz, 1H) 7.26-7.28 (m, 1H) 7.39 (d, J=5.39 Hz, 1H) 7.81 (d, J=5.38 Hz, 1H) 7.98 (d, J=5.41 Hz, 1H) 8.23 (d, J=7.92 Hz, 1H) 9.89 (s, 1H) 11.49 (br s, 1H).

Workup

  1. custom×16 hours
  2. customThe solvent was evaporated under a nitrogen stream
  3. customthe resulting residue purified via preparative HPLC (0.1% triethylamine/1% acetonitrile mixture in water and methanol)

Sources & evidence

ORD record
ord-2b0d948df2704cd0a60e1dff7653e2b5
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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