6-Chloro-5-cyclopropylpyrimidin-4-amine → 6-{4-[1-(2-Azetidin-1-yl-ethyl)-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-cyclopropyl-pyrimidin-4-ylamine

HRID 57141Notes

Reaction equation

HRID 57141 reaction equation
Cl.Cl.Cl.[N:4]1([CH2:8][CH2:9][N:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[C:17]([CH3:22])[CH:16]=3)[N:12]=[C:11]2[CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:7][CH2:6][CH2:5]1.Cl[C:30]1[N:35]=[CH:34][N:33]=[C:32]([NH2:36])[C:31]=1[CH:37]1[CH2:39][CH2:38]1>>[N:4]1([CH2:8][CH2:9][N:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[C:17]([CH3:22])[CH:16]=3)[N:12]=[C:11]2[CH:23]2[CH2:24][CH2:25][N:26]([C:30]3[N:35]=[CH:34][N:33]=[C:32]([NH2:36])[C:31]=3[CH:37]3[CH2:39][CH2:38]3)[CH2:27][CH2:28]2)[CH2:5][CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 467398956-Chloro-5-cyclopropylpyrimidin-4-amineHCID 131736949HCID 131736949, compound

Product 1

HCID 1182903176-{4-[1-(2-Azetidin-1-yl-ethyl)-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-cyclopropyl-pyrimidin-4-ylamine

Procedure

The title compound was prepared according to the procedure described for the preparation of compound “1” by using 4-[1-(2-azetidin-1-yl-ethyl)-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl]-piperidine trihydrochloride and 6-chloro-5-cyclopropyl-pyrimidin-4-ylamine as the starting materials. LC-MS (M+H=476, obsd=476). 1H NMR (400 MHz, DMSO-d6) δ 7.92 (s, 1H), 7.66-7.56 (m, 1H), 7.55-7.49 (m, 1H), 7.47 (s, 1H), 7.07 (t, J=9.1 Hz, 1H), 6.16 (s, 2H), 4.19 (d, J=13.0 Hz, 2H), 3.88 (t, J=6.3 Hz, 2H), 3.11 (t, J=6.9 Hz, 4H), 3.05-2.86 (m, 3H), 2.69 (t, J=6.2 Hz, 2H), 2.26 (s, 3H), 1.92 (ddt, J=26.3, 10.1, 5.7 Hz, 6H), 1.49 (q, J=6.9 Hz, 1H), 1.09-0.95 (m, 2H), 0.43 (d, J=5.2 Hz, 2H).

Workup

  1. customdescribed for the preparation of compound “1”

Sources & evidence

ORD record
ord-5dae7a4f8a724da0aba68a44b2719065
Source dataset
uspto-grants-2016_09
Patent number
US09434714B2

Reaction notes

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