Diisopropylethylamine → HCID 178493851, compound

HRID 1259502Notes

Reaction equation

HRID 1259502 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]3[C:17]4[N:18]([CH2:26][CH2:27][N:28]=4)[C:19]([NH2:25])=[N:20][C:21]=3[C:22]=2[O:23][CH3:24])[CH2:3]1.[CH3:29][C:30]1[S:31][C:32]([C:36](O)=[O:37])=[C:33]([CH3:35])[N:34]=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.CCOC(C)=O>[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]3[C:17]4[N:18]([CH2:26][CH2:27][N:28]=4)[C:19]([NH:25][C:36]([C:32]4[S:31][C:30]([CH3:29])=[N:34][C:33]=4[CH3:35])=[O:37])=[N:20][C:21]=3[C:22]=2[O:23][CH3:24])[CH2:3]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 736488Dimethyl-1,3-thiazole-5-carboxylic acidHCID 2724699PyBOPHCID 178493852HCID 178493852, compound

Product 1

HCID 178493851HCID 178493851, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-{3-[(2R,6S)-2,6-Dimethylmorpholin-4-yl]propoxy}-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine (120 mg, 0.31 mmol) was dissolved in DMF (1.5 mL), and 2,4-dimethyl-1,3-thiazole-5-carboxylic acid (58 mg, 0.37 mmol) was added. PYBOP (193 mg, 0.37 mmol) and diisopropylethylamine (0.16 mL, 0.93 mmol) were subsequently added, and the mixture was stirred at room temperature overnight. EtOAc was added, and the precipitate was isolated by vacuum filtration to give the title compound (131 mg, 80%): HPLC MS RT=2.05 min, MH+=527.1; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 8.02 (1H, d), 7.43 (1H, d), 4.38 (2H, m), 4.32 (2H, m), 4.22 (2H, m), 4.00 (3H, s), 3.81 (2H, m), 3.53 (2H, d), 3.28 (2H, m), 2.72-2.63 (8H, m), 2.26 (2H, m), 1.13 (6H, d).

Workup

  1. customthe precipitate was isolated by vacuum filtration

Sources & evidence

ORD record
ord-e75ed70c12f54f4f88337215446afb00
Source dataset
uspto-grants-2013_06
Patent number
US08466283B2

Reaction notes

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