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

HRID 57142Notes

Reaction equation

HRID 57142 reaction equation
[N:1]1([CH2:5][CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([CH:18]([CH3:20])[CH3:19])[CH:13]=3)[N:9]=[C:8]2[CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:4][CH2:3][CH2:2]1.Cl[C:28]1[N:33]=[CH:32][N:31]=[C:30]([NH2:34])[C:29]=1[CH:35]1[CH2:37][CH2:36]1>>[N:1]1([CH2:5][CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([CH:18]([CH3:20])[CH3:19])[CH:13]=3)[N:9]=[C:8]2[CH:21]2[CH2:22][CH2:23][N:24]([C:28]3[N:33]=[CH:32][N:31]=[C:30]([NH2:34])[C:29]=3[CH:35]3[CH2:37][CH2:36]3)[CH2:25][CH2:26]2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 467398956-Chloro-5-cyclopropylpyrimidin-4-amineHCID 894424674-[1-(2-azetidin-1-yl-ethyl)-2-piperidin-4-yl-1H-imidazol-4-yl]-2-isopropyl-pyridine

Product 1

HCID 1182903006-{4-[1-(2-Azetidin-1-yl-ethyl)-4-(2-isopropyl-pyridin-4-yl)-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)-2-piperidin-4-yl-1H-imidazol-4-yl]-2-isopropyl-pyridine and 6-chloro-5-cyclopropyl-pyrimidin-4-ylamine as the starting materials. LC-MS (M+H=487, obsd=487). 1H NMR (400 MHz, DMSO-d6) δ 8.38 (d, J=5.2 Hz, 1H), 7.92 (s, 1H), 7.81 (s, 1H), 7.52 (s, 1H), 7.46 (d, J=5.2 Hz, 1H), 6.17 (s, 2H), 4.19 (d, J=12.9 Hz, 2H), 3.92 (t, J=6.1 Hz, 2H), 3.12 (t, J=6.7 Hz, 4H), 3.05-2.88 (m, 4H), 2.72 (t, J=6.1 Hz, 2H), 1.98-1.82 (m, 6H), 1.50 (p, J=6.7 Hz, 1H), 1.25 (dd, J=6.9, 1.3 Hz, 6H), 1.02 (d, J=8.1 Hz, 2H), 0.43 (d, J=5.2 Hz, 2H).

Workup

  1. customdescribed for the preparation of compound “1”

Sources & evidence

ORD record
ord-7a077d6abced4fc0a80a6934746c2aec
Source dataset
uspto-grants-2016_09
Patent number
US09434714B2

Reaction notes

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