Acetic Anhydride → N-{[3-({[2-(1,1-D ioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]amino}methyl)oxetan-3-yl]methyl}acetamide

HRID 540222Notes

Reaction equation

[NH2:1][CH2:2][C:3]1([CH2:7][NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=3)[N:12]=[C:11]([N:20]3[CH2:26][C:25]4[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=4[S:23](=[O:32])(=[O:31])[CH2:22][CH2:21]3)[CH:10]=2)[CH2:6][O:5][CH2:4]1.[C:33](OC(=O)C)(=[O:35])[CH3:34]>>[O:31]=[S:23]1(=[O:32])[C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[CH2:26][N:20]([C:11]2[CH:10]=[C:9]([NH:8][CH2:7][C:3]3([CH2:2][NH:1][C:33](=[O:35])[CH3:34])[CH2:6][O:5][CH2:4]3)[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=3)[N:12]=2)[CH2:21][CH2:22]1

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 71262358N-{[3-(Aminomethyl)oxetan-3-yl]methyl}-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-amine

Product 1

HCID 71262230N-{[3-({[2-(1,1-D ioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]amino}methyl)oxetan-3-yl]methyl}acetamide

Procedure

The title compound was prepared in analogy to Example 63-1 in Scheme 25 by using N-{[3-(aminomethyl)oxetan-3-yl]methyl}-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-amine (prepared in analogy to Example 3-50) and acetic anhydride. MS obsd. (ESI+) [(M+H)+] 495, 1H NMR (400 MHz, CD3OD) δ ppm 8.00 (d, J=7.6 Hz, 1 H), 7.89 (d, J=7.2 Hz, 1 H), 7.66 (t, 2 H), 7.46 (t, 2 H), 7.32-7.30 (m, 1 H), 6.22 (s, 1 H), 5.17 (s, 2 H), 4.56-4.51 (m, 6 H), 3.67 (d, 4 H), 3.60 (t, J=9.6 Hz, 2 H), 2.43 (s, 3 H), 2.06 (s, 3 H).

Sources & evidence

ORD record: ord-e1065a1866054f328a9145aa4cb28303
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871756B2

Reaction notes

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