4-Isopropylaniline → HCID 71735529, compound

HRID 338687Notes

Reaction equation

HRID 338687 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:11][N:10]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=3)[C:15](O)=[O:16])[CH2:9][CH2:8][C:6]=2[N:7]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:54]([C:57]1[CH:63]=[CH:62][C:60]([NH2:61])=[CH:59][CH:58]=1)([CH3:56])[CH3:55].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:11][N:10]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=3)[C:15]([NH:61][C:60]3[CH:62]=[CH:63][C:57]([CH:54]([CH3:56])[CH3:55])=[CH:58][CH:59]=3)=[O:16])[CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

8

Reactant 5

HCID 74644-IsopropylanilineHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866958153-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzoic acid

Product 1

HCID 71735529HCID 71735529, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzoic acid (41 mg, 0.15 mmol), N,N-diisopropylethylamine (0.105 mL, 0.60 mmol), and HBTU (63 mg, 0.165 mmol) in 1.5 mL DMF was briefly warmed to approx. 50° C. to dissolve solids, then continued stirring at room temperature. After 10 minutes 4-isopropylaniline (0.032 mL, 0.225 mmol) was added and the reaction continued at room temperature for 18 hours. The reaction was added drop wise to a stirring mixture of 35 mL water containing 4 mL brine and 0.3 mL saturated aqueous Na2CO3 solution at room temperature. The resulting precipitate was filtered and rinsed with water. The damp solid was dissolved in 40% MeOH in CHCl3 and evaporated to a dry solid. The solid was triturated with an acetone/hexane mixture to give the title compound as a light beige solid (44 mg, 75%). 1H NMR (DMSO-d6) δ: 10.08 (s, 1H), 8.13 (s, 1H), 7.64-7.70 (m, 2H), 7.49-7.51 (m, 1H), 7.31-7.40 (m, 2H), 7.18-7.25 (m, 3H), 6.40 (s, 2H), 4.29 (s, 2H), 3.65 (t, J=6.0 Hz, 2H), 2.81-2.94 (m, 1H), 2.77 (t, J=5.9 Hz, 2H), 1.20 (d, J=7.0 Hz, 6H).

Workup

  1. dissolutionto dissolve solids
  2. additionThe reaction was added drop
  3. filtrationThe resulting precipitate was filtered
  4. washrinsed with water
  5. dissolutionThe damp solid was dissolved in 40% MeOH in CHCl3
  6. customevaporated to a dry solid
  7. customThe solid was triturated with an acetone/hexane mixture

Sources & evidence

ORD record
ord-0b37238a610949a8bfd21bf7df5338d0
Source dataset
uspto-grants-2014_11
Patent number
US08889870B2

Reaction notes

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