2,4-Dichloro-6-methylquinazoline → N-{[3-(Benzylamino)oxetan-3-yl]methyl}-6-methyl-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinazolin-4-amine

HRID 540193Notes

Reaction equation

HRID 540193 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.[NH2:14][CH2:15][C:16]1([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:19][O:18][CH2:17]1.[S:28]1(=[O:39])[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[CH2:32][NH:31][CH2:30][CH2:29]1>>[CH2:21]([NH:20][C:16]1([CH2:15][NH:14][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=3)[N:3]=[C:2]([N:31]3[CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[S:28](=[O:39])[CH2:29][CH2:30]3)[N:11]=2)[CH2:19][O:18][CH2:17]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 142564832,4-Dichloro-6-methylquinazolineHCID 196082032,3,4,5-Tetrahydrobenzo[f][1,4]thiazepine 1-oxideHCID 574158553-(aminomethyl)-N-benzyloxetan-3-amine

Product 1

HCID 86691402N-{[3-(Benzylamino)oxetan-3-yl]methyl}-6-methyl-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinazolin-4-amine

Procedure

The title compound was prepared in analogy to Example 55-1 in Scheme 23 by using 2,4-dichloro-6-methylquinazoline, 3-(aminomethyl)-N-benzyloxetan-3-amine and 2,3,4,5-tetrahydro-1,4-benzothiazepine 1-oxide. MS obsd. (ESI+) [(M+H)+] 514, 1H NMR (400 MHz, CD3OD) δ ppm 8.06 (s, 1 H), 7.81-7.77 (m, 2 H), 7.66-7.56 (m, 4 H), 7.47-7.45 (m, 2 H), 7.31-7.29 (m, 3 H), 5.45-5.35 (d, 1 H), 5.10 (brs, 1 H), 4.82-4.80 (m, 6 H), 4.71-4.69 (m, 2 H), 4.16 (s, 2 H), 3.51 (m, 2 H), 2.46 (s, 3 H).

Sources & evidence

ORD record
ord-c45fc820a5b04cd88737c8551f417cc5
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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