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

HRID 1910443Notes

Reaction equation

HRID 1910443 reaction equation
Cl[C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH2:12]([NH2:16])[CH2:13][CH2:14][NH2:15].[NH:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][NH:20][CH2:19][CH2:18]1>>[NH:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][N:20]([C:2]2[N:3]=[C:4]([NH:15][CH2:14][CH2:13][CH2:12][NH2:16])[C:5]3[S:10][CH:9]=[CH:8][C:6]=3[N:7]=2)[CH2:19][CH2:18]1

Participants

4

Reactant 3

HCID 4281,3-PropanediamineHCID 27717622,3,4,5-tetrahydro-1H-1,4-benzodiazepineHCID 127128322,4-Dichlorothieno[3,2-d]pyrimidine

Product 1

HCID 71548936N-[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-dichlorothieno[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)+] 355, 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.71 (d, J=5.6 Hz, 1H), 7.37 (d, J=7.1 Hz, 1H), 7.08 (d, J=5.3 Hz, 1H), 7.02-7.07 (m, 1H), 6.79-6.86 (m, 2H), 4.85 (s, 2H), 4.04-4.09 (m, 2H), 3.73 (t, J=6.6 Hz, 2H), 3.20-3.24 (m, 2H), 2.86-2.92 (m, 2H), 1.93-2.03 (m, 2H).

Sources & evidence

ORD record
ord-124a550d10074128a1c7a0df009ebf58
Source dataset
uspto-grants-2013_12
Patent number
US08604019B2

Reaction notes

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