[3-(Aminomethyl)oxetan-3-yl]methanamine → N-{[3-(Aminomethyl)oxetan-3-yl]methyl}-2-(2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinazolin-4-amine

HRID 540220Notes

Reaction equation

HRID 540220 reaction equation
Cl[C:2]1[NH:11][C:10](=O)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1.[S:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][NH:17][CH2:16][CH2:15]1.[O:25]1[CH2:28][C:27]([CH2:31][NH2:32])([CH2:29][NH2:30])[CH2:26]1>>[NH2:30][CH2:29][C:27]1([CH2:31][NH:32][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=3)[N:3]=[C:2]([N:17]3[CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[S:14][CH2:15][CH2:16]3)[N:11]=2)[CH2:28][O:25][CH2:26]1

Participants

4

Reactant 3

HCID 10953471[3-(Aminomethyl)oxetan-3-yl]methanamineHCID 122691062,3,4,5-Tetrahydrobenzo[f][1,4]thiazepineHCID 1355887902-Chloro-6-methyl-3,4-dihydroquinazolin-4-one

Product 1

HCID 71254477N-{[3-(Aminomethyl)oxetan-3-yl]methyl}-2-(2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinazolin-4-amine

Procedure

The title compound was prepared in analogy to Example 62-1 in Scheme 23 by using 2-chloro-6-methylquinazolin-4(3H)-one, 2,3,4,5-tetrahydro-1,4-benzothiazepine and oxetane-3,3-diyldimethanamine. MS obsd. (ESI+) [(M+H)+] 422. 1H NMR (400 MHz, CD3OD) δ ppm 7.66 (dd, J=1.6, 7.2 Hz, 1 H), 7.62 (s, 1 H), 7.44 (dd, J=1.2, 7.6 Hz, 1 H), 7.34-7.29 (m, 2 H), 7.18 (m, 1 H), 7.08 (m, 1 H), 4.99 (s, 2 H), 4.63 (d, J=6.4 Hz, 2 H), 4.45 (d, J=6.4 Hz, 2 H), 4.34 (s, 2 H), 4.02 (s, 2 H), 2.98 (s, 2 H), 2.90 (m, 2 H), 2.36 (s, 3 H).

Sources & evidence

ORD record
ord-15a8a58595c74e4390653b78be3f6c6a
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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