4-(3-Hydroxypropyl)thiomorpholine 1,1-Dioxide → 8-[3-(1,1-dioxo-1,4-thiazinan-4-yl)propoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine

HRID 536249Notes

Reaction equation

HRID 536249 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:14]([CH2:22][CH2:23][N:24]=3)[C:15]([NH2:21])=[N:16][C:17]=2[C:18]=1[O:19][CH3:20])[C:2]1[CH:7]=CC=CC=1.[O:25]=[S:26]1(=[O:36])[CH2:31][CH2:30][N:29](CCCO)[CH2:28][CH2:27]1>>[O:25]=[S:26]1(=[O:36])[CH2:31][CH2:30][N:29]([CH2:7][CH2:2][CH2:1][O:8][C:9]2[CH:10]=[CH:11][C:12]3[C:13]4[N:14]([CH2:22][CH2:23][N:24]=4)[C:15]([NH2:21])=[N:16][C:17]=3[C:18]=2[O:19][CH3:20])[CH2:28][CH2:27]1

Participants

3

Reactant 2

HCID 114354734-(3-Hydroxypropyl)thiomorpholine 1,1-DioxideHCID 1784938207-methoxy-8-phenylmethoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine2×

Product 1

HCID 1784938658-[3-(1,1-dioxo-1,4-thiazinan-4-yl)propoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine

Procedure

The procedure used for the preparation of Example 4 was used to prepare the title compound from 5-amino-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-8-ol bistrifluoroacetate salt (Intermediate A) and 3-(1,1-dioxidothiomorpholin-4-yl)propan-1-ol. High vacuum drying gave the title compound (1.48 g, 83%): HPLC MS RT=0.26 min, MH+=408.3; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 2.23-2.25 (2H, m), 3.43-3.48 (2H, m), 3.81-3.84 (7H, m), 4.19-4.22 (2H, m), 4.27 (2H, t), 4.33-4.36 (2H, m), 7.30 (1H, d), 7.92 (1H, d).

Workup

  1. customThe procedure used for the preparation of Example 4

Sources & evidence

ORD record
ord-114f8594ad5d42d09d9c41a3783855f5
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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