Diisopropylethylamine → HCID 58110170, compound

HRID 1803274Notes

Reaction equation

N1(O[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([C:23]2[NH:27][N:26]=[C:25]([NH:28][C:29]3[CH:30]=[N:31][C:32]([N:37]4[CH:41]=[C:40]([Cl:42])[N:39]=[CH:38]4)=[C:33]([O:35][CH3:36])[CH:34]=3)[N:24]=2)[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CC(=O)CC>[Cl:42][C:40]1[N:39]=[CH:38][N:37]([C:32]2[N:31]=[CH:30][C:29]([NH:28][C:25]3[N:24]=[C:23]4[CH:15]([C:16]5[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=5)[CH2:14][CH2:13][CH2:12][CH2:11][N:27]4[N:26]=3)=[CH:34][C:33]=2[O:35][CH3:36])[CH:41]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A microwave vial was charged with N-(5-(5-(1H-benzo[d][1,2,3]triazol-1-yloxy)-1-(4-fluorophenyl)pentyl)-1H-1,2,4-triazol-3-yl)-6-(4-chloro-1H-imidazol-1-yl)-5-methoxypyridin-3-amine (300 mg, 0.509 mmol), DIEA (0.089 mL, 0.509 mmol), and 2-butanone (5 mL). The mixture was heated in a microwave at 180° C. for 4 h. The reaction mixture was concentrated in vacuo. The crude product was purified using silica gel column chromatography (10-80% EtOAc/chloroform, linear gradient) to afford N-(6-(4-chloro-1H-imidazol-1-yl)-5-methoxypyridin-3-yl)-9-(4-fluorophenyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[1,5-a]azepin-2-amine (13 mg, 0.029 mmol, 6% yield) as white solid. LC-MS (M+H)+ 454.2. 1H NMR (500 MHz, chloroform-d) δ ppm 8.13 (d, J=1.53 Hz, 1 H) 8.03 (d, J=2.44 Hz, 1 H) 7.82 (d, J=2.44 Hz, 1 H) 7.58 (d, J=1.83 Hz, 1 H) 7.13-7.21 (m, 2H) 7.06 (t, J=8.70 Hz, 2H) 6.77 (s, 1 H) 4.16-4.34 (m, 3 H) 3.88 (s, 3 H) 1.78-2.28 (m, 6 H).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customThe crude product was purified

Sources & evidence

ORD record: ord-75310d2c3a184b17836c13e626f63594
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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