HCID 55281927, compound → HCID 58199531, compound

HRID 2406142Notes

Reaction equation

[C:1]([NH:3][C:4](=[N:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:15][CH:14]=1)OC1C=CC=CC=1)#[N:2].[NH:27]([C:29]1[C:30]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][C:31]=2[N:32]=[CH:33][N:34]=1)[NH2:28]>C(O)(C)C>[N:32]1[C:31]2[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:30]=2[C:29]([N:27]2[C:1]([NH2:2])=[N:3][C:4]([NH:12][C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]4[CH2:23][CH2:24][CH2:25][CH2:26]4)=[CH:17][CH:18]=3)=[N:28]2)=[N:34][CH:33]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of N-cyano-N′-{[4-(pyrrolidin-1-yl-ethoxy)]phenyl}-O-phenylisourea (50 mg; 0.14 mmol; 1.0 equiv) and 4-hydrazino-5,6,7,8,9,10-hexahydrocycloocta[d]-pyrimidine (28 mg; 0.14 mmol; 1 equiv) in 1 mL of isopropanol was heated in the microwave apparatus at 150° C. for 15 min. Purification by silica gel column chromatography eluted with CH2Cl2/MeOH/Et3N (95/5/1) gave 1-(5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidin-4-yl)-N3-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-1H-1,2,4-triazole-3,5-diamine, compound #20, as a pale-yellow solid (50 mg; 78% yield); 1H-NMR (DMSO-d6, 300 MHz) 8.85 (br. s, 1H), 8.71 (s, 1H), 7.53 (br. s, 2H), 7.43 (d, J=9.0 Hz, 2H), 6.83 (d, J=8.7 Hs, 2H), 4.05-3.98 (m, 2H), 3.40-3.22 (m, 4H), 3.00-2.95 (m, 2H), 2.72-2.58 (m, 4H), 1.92-1.83 (m, 2H), 1.78-1.68 (m, 6H), 1.48-1.32 (m, 4H) ppm; MS (ES) 449.54 (M+H), 447.25 (M−H).

Workup

customPurification by silica gel column chromatography
washeluted with CH2Cl2/MeOH/Et3N (95/5/1)

Sources & evidence

ORD record: ord-e3bd29a92f554257a368eb99b71d2b6c
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809347B2

Reaction notes

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