Dimethylformamide → HCID 86710178, compound

HRID 2284410Notes

Reaction equation

HRID 2284410 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:5]2[N:11]=[CH:10][C:9]([C:12]3[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=3)=[CH:8][C:6]=2[N:7]=1.[CH:27]1([NH2:30])[CH2:29][CH2:28]1.CN(C=O)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CO.C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)[C:5]2[N:11]=[CH:10][C:9]([C:12]3[CH:20]=[CH:19][C:15]([C:16]([NH:30][CH:27]4[CH2:29][CH2:28]4)=[O:17])=[CH:14][CH:13]=3)=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 69828CyclopropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86710177HCID 86710177, compound

Product 1

HCID 86710178HCID 86710178, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a 50 mL round bottom flask, 4-(2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-7-yl)benzoic acid (0.2 g, 0.00054 mol), cyclopropyl amine (0.046 g, 0.00081 mol) and DMF (10 mL) were added. To the same flask, HATU (0.3 g, 0.00081 mol) and TEA (0.23 mL, 0.0018 mol) were added. The reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with 10% methanol in chloroform and washed with water. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to provide the crude product. The crude product was purified by flash column chromatography (0-1% methanol in chloroform) to provide the title compound (0.15 g, 68%). 1H NMR (300 MHz, DMSO-d6): δ 9.21 (d, J=2.4 Hz, 1H), 8.59 (d, J=4.2 Hz, 1H), 8.42 (d, J=2.4 Hz, 1H), 7.94-8.06 (m, 4H), 4.52 (br s, 4H), 3.80 (t, J=4.8 Hz, 4H), 2.88-2.90 (m, 1H), 0.60-0.62 (m, 2H), 0.70-0.73 (m, 2H): LC-MS (ESI): Calculated mass: 409.1; Observed mass [M+H]+: 410.1. (RT=1.34 min).

Workup

  1. washwashed with water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customto provide the crude product
  6. customThe crude product was purified by flash column chromatography (0-1% methanol in chloroform)

Sources & evidence

ORD record
ord-9b8936b912674c94828072e3a1d152ed
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

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