(R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine → (4-chlorophenyl)(7-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)methanamine bishydrochloride

HRID 521371Notes

Reaction equation

HRID 521371 reaction equation
[Cl:1][C:2]1[C:3]2[C@H:10]([CH3:11])[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.Cl.Cl.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([C:23]2[N:27]3[CH2:28][CH2:29][NH:30][CH2:31][C:26]3=[N:25][N:24]=2)[NH2:22])=[CH:17][CH:16]=1>>[ClH:1].[ClH:14].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([C:23]2[N:27]3[CH2:28][CH2:29][N:30]([C:2]4[C:3]5[C@H:10]([CH3:11])[CH2:9][CH2:8][C:4]=5[N:5]=[CH:6][N:7]=4)[CH2:31][C:26]3=[N:25][N:24]=2)[NH2:22])=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 59670769(R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidineHCID 67436165HCID 67436165, compound

Product 1

HCID 67438712(4-chlorophenyl)(7-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)methanamine bishydrochlorideYield 64%

Procedure

Using the procedure from Example 8, Step 5, using (R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine and (4-chlorophenyl)(5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)methanamine bishydrochloride (100 mg, 0.30 mmol) to afford (4-chlorophenyl)(7-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)methanamine bishydrochloride (75 mg, 0.19 mmol, 64%): LCMS APCI+(M+H+): 396 (60%), 398 (20%), rt 2.48 min. HPLC purity at 254 nm >99%, rt=1.68 min. 1H NMR (400 MHz, d6-DMSO) □ 9.51 (s, 3H), 8.85 (d, J=9.4 Hz, 1H), 7.61 (d, J=7.0 Hz, 2H), 7.55 (d, J=7.8 Hz, 2H), 6.08 (br d, J=9.0 Hz, 1H), 5.42 (dd, J=26 Hz, 16 Hz, 1H), 5.19 (dd, J=21 Hz, 18 Hz, 1H), 4.55 (m, 1H), 4.29 (m, 1H), 3.79 (m, 1H), 3.14 (m, 1H), 2.96 (m, 1H), 2.32 (m, 1H), 1.82 (m, 1H), 1.15 (t, J=6.8 Hz, 2H), 1.04 (d, J=6.2 Hz, 3H).

Sources & evidence

ORD record
ord-f74b21b22544486bb07dd91e5fca7242
Source dataset
uspto-grants-2016_05
Patent number
US09328091B2

Reaction notes

Loading…