Nicotinic Acid → HCID 178493850, compound

HRID 1259501Notes

Reaction equation

HRID 1259501 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.[C:29](O)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=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:29](=[O:36])[C:30]4[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=4)=[N:20][C:21]=3[C:22]=2[O:23][CH3:24])[CH2:3]1

Participants

7

Reactant 4

HCID 938Nicotinic AcidHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 178493852HCID 178493852, compound

Product 1

HCID 178493850HCID 178493850, compoundYield 61%

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 (200 mg, 0.52 mmol) was dissolved in DMF (2.0 mL), and nicotinic acid (76 mg, 0.62 mmol) was added. PYBOP (322 mg, 0.62 mmol) and diisopropylethylamine (0.33 mL, 1.55 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 (156 mg, 61%): HPLC MS RT=1.34 min, MH+=493.3; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 9.53 (1H, s), 9.03 (1H, d), 9.00 (1H, d), 8.07 (1H, d), 8.01 (1H, dd), 7.49 (1H, d), 4.58 (2H, m), 4.34 (2H, t), 4.27 (2H, m), 4.03 (3H, s), 3.81 (2H, m), 3.53 (2H, d), 3.29 (2H, m), 2.69 (2H, m), 2.27 (2H, m), 1.15 (6H, d).

Workup

  1. customthe precipitate was isolated by vacuum filtration

Sources & evidence

ORD record
ord-0b693f68752049fa88fc123ff93007bd
Source dataset
uspto-grants-2013_06
Patent number
US08466283B2

Reaction notes

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