2,4,6-Trichloroquinazoline → N-{[3-(aminomethyl)oxetan-3-yl]methyl}-6-chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinazolin-4-amine

HRID 540198Notes

Reaction equation

HRID 540198 reaction equation
Cl[C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:13])[CH:8]=2)[N:3]=1.[O:14]1[CH2:17][C:16]([CH2:20][NH2:21])([CH2:18][NH2:19])[CH2:15]1.[S:22]1(=[O:34])(=[O:33])[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[CH2:26][NH:25][CH2:24][CH2:23]1>>[NH2:19][CH2:18][C:16]1([CH2:20][NH:21][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([Cl:13])[CH:8]=3)[N:3]=[C:2]([N:25]3[CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[S:22](=[O:34])(=[O:33])[CH2:23][CH2:24]3)[N:11]=2)[CH2:17][O:14][CH2:15]1

Participants

4

Reactant 3

HCID 104215102,4,6-TrichloroquinazolineHCID 10953471[3-(Aminomethyl)oxetan-3-yl]methanamineHCID 196081962,3,4,5-Tetrahydrobenzo[F][1,4]thiazepine 1,1-dioxide

Product 1

HCID 71255174N-{[3-(aminomethyl)oxetan-3-yl]methyl}-6-chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinazolin-4-amine

Procedure

The title compound was prepared in analogy to Example 56-1 in Scheme 23 by using 2,4,6-trichloroquinazoline, oxetane-3,3-diyldimethanamine and 2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide. MS obsd. (ESI+) [(M+H)+] 474, 1H NMR (400 MHz, CD3OD) δ ppm 7.99 (d, J=6.82 Hz, 1 H), 7.94 (d, J=2.53 Hz, 1 H), 7.88 (d, J=7.07 Hz, 1 H), 7.66-7.59 (m, 1 H), 7.52-7.42 (m, 2 H), 7.42-7.36 (m, 1 H), 5.21 (brs, 2 H), 4.69-4.56 (m, 5 H), 4.51 (d, J=6.32 Hz, 2 H), 4.05 (brs, 2 H), 3.52 (t, J=5.05 Hz, 2 H), 3.04 (s, 2 H).

Sources & evidence

ORD record
ord-b9d900bf164f4515b87dc6afcec06456
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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