2,4,6-Trichloroquinazoline → N-[(3-Aminooxetan-3-yl)methyl]-6-chloro-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinazolin-4-amine

HRID 540207Notes

Reaction equation

HRID 540207 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.[NH2:14][CH2:15][C:16]1([NH2:20])[CH2:19][O:18][CH2:17]1.[S:21]1(=[O:32])[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH2:25][NH:24][CH2:23][CH2:22]1>>[NH2:20][C:16]1([CH2:15][NH:14][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([Cl:13])[CH:8]=3)[N:3]=[C:2]([N:24]3[CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[S:21](=[O:32])[CH2:22][CH2:23]3)[N:11]=2)[CH2:19][O:18][CH2:17]1

Participants

4

Reactant 3

HCID 104215102,4,6-TrichloroquinazolineHCID 196082032,3,4,5-Tetrahydrobenzo[f][1,4]thiazepine 1-oxideHCID 217130163-(Aminomethyl)oxetan-3-amine

Product 1

HCID 71262224N-[(3-Aminooxetan-3-yl)methyl]-6-chloro-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 57-1 in Scheme 23 by using 2,4,6-trichloroquinazoline, 3-(aminomethyl)oxetan-3-amine and 2,3,4,5-tetrahydro-1,4-benzothiazepine 1-oxide. MS obsd. (ESI+) [(M+H)+] 444, 1H NMR (400 MHz, CD3OD) δ ppm 8.57 (s, 1 H), 8.01-7.73 (m, 2 H), 7.52-7.40 (m, 4 H), 5.31-5.28 (d, J=15.2 Hz, 1 H), 4.66-4.53 (m, 6 H), 4.08 (s, 2 H), 3.51-3.50 (m, 2 H), 1.36-1.31 (m, 1 H).

Sources & evidence

ORD record
ord-7396cba22d794008b3ecc2b9f9941170
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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