2,4-Dichloro-6-methylquinazoline → 2-Fluoro-N-[6-methyl-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinazolin-4-yl]propane-1,3-diamine

HRID 540194Notes

Reaction equation

HRID 540194 reaction equation
Cl[C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1.[F:14][CH:15]([CH2:18][NH2:19])[CH2:16][NH2:17].[S:20]1(=[O:31])[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[CH2:24][NH:23][CH2:22][CH2:21]1>>[F:14][CH:15]([CH2:18][NH2:19])[CH2:16][NH:17][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=[C:2]([N:23]2[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[S:20](=[O:31])[CH2:21][CH2:22]2)[N:11]=1

Participants

4

Reactant 3

HCID 142564832,4-Dichloro-6-methylquinazolineHCID 196082032,3,4,5-Tetrahydrobenzo[f][1,4]thiazepine 1-oxideHCID 199026462-Fluoropropane-1,3-diamine

Product 1

HCID 712621332-Fluoro-N-[6-methyl-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinazolin-4-yl]propane-1,3-diamine

Procedure

The title compound was prepared in analogy to Example 55-1 in Scheme 23 by using 2,4-dichloro-6-methylquinazoline, 2-fluoropropane-1,3-diamine and 2,3,4,5-tetrahydro-1,4-benzothiazepine 1-oxide. MS obsd. (ESI+) [(M+H)+] 414, 1H NMR (400 MHz, CD3OD) δ ppm (d, J=7.6 Hz, 1 H), 7.79 (s, 1 H), 7.70-7.20 (m, 6 H), 5.56 (m, 1 H), 4.85-4.55 (m, 3 H), 4.48-4.32 (brs, 1 H), 3.91-3.71 (brs, 2 H), 3.40-3.11 (m, 2 H), 2.93-2.72 (m, 2 H), 2.24 (s, 3 H), 1.68 (s, 2 H).

Sources & evidence

ORD record
ord-6d03960d20454c85b2788e4d24f65c1f
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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