2,3,4,5-Tetrahydrobenzo[f][1,4]thiazepine → N-[2-(2,3-Dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinazolin-4-yl]-2,2-difluoropropane-1,3-diamine

HRID 540195Notes

Reaction equation

HRID 540195 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.[F:14][C:15]([F:20])([CH2:18][NH2:19])[CH2:16][NH2:17].[S:21]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH2:25][NH:24][CH2:23][CH2:22]1>>[S:21]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH2:25][N:24]([C:2]2[N:11]=[C:10]([NH:17][CH2:16][C:15]([F:20])([F:14])[CH2:18][NH2:19])[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=3)[N:3]=2)[CH2:23][CH2:22]1

Participants

4

Reactant 3

HCID 122691062,3,4,5-Tetrahydrobenzo[f][1,4]thiazepineHCID 142564832,4-Dichloro-6-methylquinazolineHCID 199026522,2-Difluoropropane-1,3-diamine

Product 1

HCID 71254462N-[2-(2,3-Dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinazolin-4-yl]-2,2-difluoropropane-1,3-diamine

Procedure

The title compound was prepared in analogy to Example 55-1 in Scheme 23 by using 2,4-dichloro-6-methylquinazoline, 2,2-difluoropropane-1,3-diamine and 2,3,4,5-tetrahydro-1,4-benzothiazepine. MS obsd. (ESI+) [(M+H)+] 416, 1H NMR (400 MHz, CD3OD) δ ppm 7.96 (s, 1 H), 7.80-7.68 (m, 1 H), 7.60-7.58 (m, 2 H), 7.51-7.49 (m, 1 H), 7.30-7.27 (t, 1 H), 7.24-7.20 (t, 1 H), 5.15 (s, 2 H), 4.37-4.31 (m, 4 H), 3.51-3.49 (m, 4 H), 3.14 (s, 2 H), 2.45 (s, 3 H).

Sources & evidence

ORD record
ord-214718849e4b45cb9056c117c6b1b927
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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