2,4-Dichloroquinazoline → N-[(3-Aminooxetan-3-yl)methyl]-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinazolin-4-amine

HRID 540205Notes

Reaction equation

HRID 540205 reaction equation
Cl[C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:13][CH2:14][C:15]1([NH2:19])[CH2:18][O:17][CH2:16]1.[S:20]1(=[O:32])(=[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>>[NH2:19][C:15]1([CH2:14][NH:13][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([N:23]3[CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[S:20](=[O:32])(=[O:31])[CH2:21][CH2:22]3)[N:11]=2)[CH2:18][O:17][CH2:16]1

Participants

4

Reactant 3

HCID 2528862,4-DichloroquinazolineHCID 196081962,3,4,5-Tetrahydrobenzo[F][1,4]thiazepine 1,1-dioxideHCID 217130163-(Aminomethyl)oxetan-3-amine

Product 1

HCID 86691407N-[(3-Aminooxetan-3-yl)methyl]-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 57-1 in Scheme 23 by using 2,4-dichloroquinazoline, 3-(aminomethyl)oxetan-3-amine and 2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide. MS obsd. (ESI+) [(M+H)+] 426, 1H NMR (400 MHz, CD3OD) δ ppm 7.98-7.93 (m, 1 H), 7.91-7.88 (m, 2 H), 7.64-7.60 (m, 1 H), 7.57-7.51 (m, 1 H), 7.48-7.41 (m, 2 H), 7.15-7.11 (m, 1 H), 5.24 (s, 2 H), 4.67-4.54 (m, 6 H), 4.09 (s, 2 H), 3.55-3.50 (m, 2 H).

Sources & evidence

ORD record
ord-b260a617b8d847498a64f8a5f707e2d6
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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