5,6-Dichloro-pyrimidin-4-ylamine → 6-{4-[1-(2-Azetidin-1-yl-ethyl)-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-chloro-pyrimidin-4-ylamine

HRID 57128Notes

Reaction equation

HRID 57128 reaction equation
Cl.[N:2]1([CH2:6][CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[C:15]([CH3:20])[CH:14]=3)[N:10]=[C:9]2[CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:5][CH2:4][CH2:3]1.[Cl:27][C:28]1[C:29]([NH2:35])=[N:30][CH:31]=[N:32][C:33]=1Cl>>[N:2]1([CH2:6][CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[C:15]([CH3:20])[CH:14]=3)[N:10]=[C:9]2[CH:21]2[CH2:22][CH2:23][N:24]([C:33]3[N:32]=[CH:31][N:30]=[C:29]([NH2:35])[C:28]=3[Cl:27])[CH2:25][CH2:26]2)[CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 1182903114-[1-(2-azetidin-1-yl-ethyl)-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl]-piperidine hydrochloride

Product 1

HCID 918273936-{4-[1-(2-Azetidin-1-yl-ethyl)-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-chloro-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 hydrochloride and 5,6-dichloro-pyrimidin-4-ylamine as starting materials. LC-MS (M+H=471, obsd=471). 1H NMR (400 MHz, DMSO-d6) δ 8.00 (s, 1H), 7.66-7.58 (m, 1H), 7.53 (ddd, J=7.8, 5.0, 2.3 Hz, 1H), 7.47 (s, 1H), 7.06 (dd, J=9.7, 8.6 Hz, 1H), 6.79 (s, 2H), 4.13 (d, J=13.0 Hz, 2H), 3.88 (t, J=6.2 Hz, 2H), 3.11 (t, J=6.9 Hz, 4H), 3.07-2.93 (m, 3H), 2.69 (t, J=6.1 Hz, 2H), 2.29-2.19 (m, 3H), 2.01-1.81 (m, 6H).

Workup

  1. customdescribed for the preparation of compound “1”

Sources & evidence

ORD record
ord-5b5d3ad276314ed1be6c681646f824e6
Source dataset
uspto-grants-2016_09
Patent number
US09434714B2

Reaction notes

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