1,3-Propanediamine → N-[6-Methyl-2-(1,2,3,5-tetrahydro-4H-1,4-benzodiazepin-4-yl)thieno[3,2-d]pyrimidin-4-yl]propane-1,3-diamine

HRID 1910442Notes

Reaction equation

HRID 1910442 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].[NH: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>>[CH3:11][C:9]1[S:10][C:5]2[C:4]([NH:16][CH2:15][CH2:14][CH2:13][NH2:17])=[N:3][C:2]([N:21]3[CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[NH:18][CH2:19][CH2:20]3)=[N:7][C:6]=2[CH:8]=1

Participants

4

Reactant 3

HCID 4281,3-PropanediamineHCID 27717622,3,4,5-tetrahydro-1H-1,4-benzodiazepineHCID 127242682,4-Dichloro-6-methylthieno[3,2-d]pyrimidine

Product 1

HCID 71548935N-[6-Methyl-2-(1,2,3,5-tetrahydro-4H-1,4-benzodiazepin-4-yl)thieno[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-1H-benzo[e][1,4]diazepine. MS obsd. (ESI+) [(M+H)+] 369, 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.35 (d, J=7.1 Hz, 1H), 7.00-7.07 (m, 1H), 6.76-6.87 (m, 3H), 4.82 (s, 2H), 4.01-4.06 (m, 2H), 3.70 (t, J=6.6 Hz, 2H), 3.18-3.23 (m, 2H), 2.87 (t, J=6.4 Hz, 2H), 2.54 (s, 3H), 1.91-1.99 (m, 2H).

Sources & evidence

ORD record
ord-4451a15c5cfb4c0d8815fbef1a1cdb99
Source dataset
uspto-grants-2013_12
Patent number
US08604019B2

Reaction notes

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