Diisopropylethylamine → HCID 178493853, compound

HRID 1259517Notes

Reaction equation

HRID 1259517 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[N:11]=[C:10]([NH2:13])[N:9]3[CH2:14][CH2:15][N:16]=[C:8]3[C:7]=2[CH:6]=[CH:5][C:4]=1[O:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.[N:27]1([CH2:32][CH2:33][C:34]2[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][N:35]=2)[CH2:31][CH2:30][CH2:29][CH2:28]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:1][O:2][C:3]1[C:12]2[N:11]=[C:10]([NH:13][C:38](=[O:39])[C:37]3[CH:41]=[CH:42][C:34]([CH2:33][CH2:32][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[N:35][CH:36]=3)[N:9]3[CH2:14][CH2:15][N:16]=[C:8]3[C:7]=2[CH:6]=[CH:5][C:4]=1[O:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 27372556-(2-(Pyrrolidin-1-yl)ethyl)nicotinic acidHCID 178493860HCID 178493860, compound

Product 1

HCID 178493853HCID 178493853, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine (150 mg, 0.21 mmol) was dissolved in DMF (2 mL), and 6-(2-pyrrolidin-1-ylethyl)nicotinic acid (92 mg, 0.42 mmol) was added. PYBOP (217 mg, 0.42 mmol) and diisopropylethylamine (73 μL, 0.42 mmol) were subsequently added, and the mixture was stirred at rt overnight. The solids that formed were isolated by vacuum filtration and washed copiously with ethyl acetate to give the title compound (81 mg, 69%): HPLC MS RT=1.05 min, MH+=562.2; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 9.30 (1H, s), 8.99 (0.5H, m), 8.50 (1H, d), 8.24 (0.5H, m), 8.06 (1H, d), 7.53 (1H, d), 7.46 (1H, d), 4.55 (2H, t), 4.35 (2H, t), 4.24 (2H, t), 4.01 (3H, s), 4.00 (2H, m), 3.68 (2H, m), 3.60 (4H, m), 3.51 (2H, m), 3.29 (4H, m), 3.11 (2H, m), 2.26 (2H, m), 2.02 (3H, m), 1.87 (3H, m).

Workup

  1. customThe solids that formed
  2. customwere isolated by vacuum filtration
  3. washwashed copiously with ethyl acetate

Sources & evidence

ORD record
ord-eb950e3dc47144edb8926a72d1087335
Source dataset
uspto-grants-2013_06
Patent number
US08466283B2

Reaction notes

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