4-(3-Hydroxypropyl)thiomorpholine 1,1-Dioxide → N-[7-[3-(1,1-dioxo-1,4-thiazinan-4-yl)propoxy]-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide

HRID 536239Notes

Reaction equation

HRID 536239 reaction equation
[OH:1][C:2]1[C:11]2[N:10]=[C:9]([NH:12][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=3)[N:8]3[CH2:21][CH2:22][N:23]=[C:7]3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[O:24]=[S:25]1(=[O:35])[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33]O)[CH2:27][CH2:26]1>>[O:35]=[S:25]1(=[O:24])[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][O:1][C:2]2[C:11]3[N:10]=[C:9]([NH:12][C:13](=[O:20])[C:14]4[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=4)[N:8]4[CH2:21][CH2:22][N:23]=[C:7]4[C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 114354734-(3-Hydroxypropyl)thiomorpholine 1,1-DioxideHCID 178522515N-(7-hydroxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyridine-3-carboxamide2×

Product 1

HCID 178522516N-[7-[3-(1,1-dioxo-1,4-thiazinan-4-yl)propoxy]-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide

Procedure

The procedure used for the preparation of Example 4 was used to prepare the title compound from N-(7-hydroxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)nicotinamide (Intermediate C) and 3-(1,1-dioxidothiomorpholin-4-yl)propan-1-ol. High vacuum drying at 60° C. gave the title compound (105 mg, 45%): HPLC MS RT=1.16 min, MH+=483.2; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 2.32-2.33 (2H, m), 3.53-3.58 (2H, m), 3.66 (4H, bs), 3.87 (4H, bs), 4.27-4.40 (2H, m), 4.58-4.65 (2H, m), 7.60 (1H, t), 7.70 (1H, d), 7.93 (1H, dd), 8.89 (1H, d), 8.99 (1H, dd), 9.50 (1H, s).

Workup

  1. customThe procedure used for the preparation of Example 4

Sources & evidence

ORD record
ord-493a6e453b694ad1aba78794bd49d7e9
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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