Hydrazine → HCID 178428329, compound

HRID 2046984Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[N:5]=[C:4]([NH:23][C:24]2[CH:29]=[C:28]([CH3:30])[C:27]([CH:31]3[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]3)=[CH:26][C:25]=2[O:38][CH:39]([CH3:41])[CH3:40])[N:3]=1.[NH2:42][NH2:43]>C(O)(C)C>[CH:39]([O:38][C:25]1[CH:26]=[C:27]([CH:31]2[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]2)[C:28]([CH3:30])=[CH:29][C:24]=1[NH:23][C:4]1[N:3]=[C:2]2[NH:42][N:43]=[C:8]([NH2:9])[C:7]2=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[N:5]=1)([CH3:41])[CH3:40]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-chloro-2-(2-isopropoxy-5-methyl-4-(1-methylpiperidin-4-yl)phenylamino)-6-(2-(isopropylsulfonyl)phenylamino)pyrimidine-5-carbonitrile (0.1 mmol) in 5 mL of isopropanol, was added hydrazine anhydrous (0.3 mmol). The solution was heated at 120° C. for 3 hours. Product was obtained after work-up and prep-HPLC. MS (ES+): 593.29 (M+1)+. 1H NMR (MeOD, 400 MHz) δ 8.01-8.03 (d, 1H), 7.83-7.86 (m, 1H), 7.31-7.43 (m, 3H), 6.91(s, 1H), 4.56-4.59 (m. 1H), 3.64-3.68 (m, 2H), 3.19-3.24 (m, 3H), 2.93(s, 3H), 2.25 (s, 3H), 2.02-2.07 (m, 4H), 1.17-1.32 (m, 12H); MS (ES+): 593.18 (M+1)+.

Workup

customProduct was obtained after work-up

Sources & evidence

ORD record: ord-81a8d4b3f42946438a34121caf4dcfdd
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592432B2

Reaction notes

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