2,3,4,5-Tetrahydrobenzo[f][1,4]thiazepine → N-[2-(2,3-Dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylthieno[3,2-d]pyrimidin-4-yl]propane-1,3-diamine

HRID 1910447Notes

Reaction equation

HRID 1910447 reaction equation
Cl[C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][C:9]([CH3:11])=[CH:8][C:6]=2[N:7]=1.[S:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH2:17][NH:16][CH2:15][CH2:14]1>>[S:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH2:17][N:16]([C:2]2[N:3]=[C:4]([NH:3][CH2:4][CH2:5][CH2:6][NH2:7])[C:5]3[S:10][C:9]([CH3:11])=[CH:8][C:6]=3[N:7]=2)[CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 122691062,3,4,5-Tetrahydrobenzo[f][1,4]thiazepineHCID 127242682,4-Dichloro-6-methylthieno[3,2-d]pyrimidine

Product 1

HCID 71548633N-[2-(2,3-Dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylthieno[3,2-d]pyrimidin-4-yl]propane-1,3-diamine

Procedure

The title compound was prepared in analogy to Example 1-1 in Scheme 1 by using 2,4-dichloro-6-methylthieno[3,2-d]pyrimidine and propane-1,3-diamne, followed by reaction with 2,3,4,5-tetrahydro-1,4-benzothiazepine. MS obsd. (ESI+) [(M+H)+] 386, 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.61-7.71 (m, 1H), 7.53 (d, J=7.6 Hz, 1H), 7.15-7.23 (m, 1H), 7.08-7.15 (m, 1H), 6.80 (s, 1H), 5.00 (s, 2H), 4.41 (br. s., 2H), 3.75 (d, J=4.0 Hz, 2H), 2.89-2.98 (m, 4H), 2.53 (s, 3H), 1.84 (m, 2H).

Sources & evidence

ORD record
ord-b3e4b9f402d4476aad0caf18b9b55918
Source dataset
uspto-grants-2013_12
Patent number
US08604019B2

Reaction notes

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