1,3-Propanediamine → N-[2-(2,3-Dihydro-1,4-benzoxazepin-4(5H)-yl)-6-methylthieno[3,2-d]pyrimidin-4-yl]propane-1,3-diamine

HRID 1910448Notes

Reaction equation

HRID 1910448 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.[CH2:13]([NH2:17])[CH2:14][CH2:15][NH2:16].[O:18]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH2:22][NH:21][CH2:20][CH2:19]1>>[O:18]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH2:22][N:21]([C:2]2[N:3]=[C:4]([NH:16][CH2:15][CH2:14][CH2:13][NH2:17])[C:5]3[S:10][C:9]([CH3:11])=[CH:8][C:6]=3[N:7]=2)[CH2:20][CH2:19]1

Participants

4

Reactant 3

HCID 4281,3-PropanediamineHCID 127242682,4-Dichloro-6-methylthieno[3,2-d]pyrimidineHCID 218827752,3,4,5-Tetrahydro-1,4-benzoxazepine

Product 1

HCID 71549075N-[2-(2,3-Dihydro-1,4-benzoxazepin-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-diamine, followed by reaction with 2,3,4,5-tetrahydro-1,4-benzoxazepine. MS obsd. (ESI+) [(M+H)+] 370; 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.43 (d, J=6.6 Hz, 1H), 7.10-7.19 (m, 1H), 6.94-7.05 (m, 2H), 6.80 (s, 1H), 4.92 (s, 2H), 4.25-4.32 (m, 2H), 4.14-4.21 (m, 2H), 3.74 (br. s., 2H), 2.96 (t, J=6.3 Hz, 2H), 2.49-2.57 (m, 3H), 1.88 (m, 2H).

Sources & evidence

ORD record
ord-2ad89051c35a439ebd7a9ad5ae97ff41
Source dataset
uspto-grants-2013_12
Patent number
US08604019B2

Reaction notes

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