Triethylamine → HCID 178462648, compound

HRID 2369834Notes

Reaction equation

C(N(CC)CC)C.[CH2:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:17]=[C:18]([NH2:23])[C:19]([NH2:22])=[CH:20][CH:21]=2)[CH2:12][CH2:11]1)[CH3:9].C(OC(=O)[NH:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:41]=[C:40]([CH:42]=O)[NH:39][N:38]=2)=[CH:33][CH:32]=1)(C)(C)C>CN(C=O)C>[CH2:8]([N:10]1[CH2:11][CH2:12][N:13]([C:16]2[CH:21]=[CH:20][C:19]3[NH:22][C:42]([C:40]4[NH:39][N:38]=[C:37]([C:34]5[CH:35]=[CH:36][C:31]([NH2:30])=[CH:32][CH:33]=5)[CH:41]=4)=[N:23][C:18]=3[CH:17]=2)[CH2:14][CH2:15]1)[CH3:9]

Participants

Conditions

Temperature: 65 °C

Procedure

Triethylamine (509 μL, 3.62 mmol) was added to a solution of 4-(4-ethylpiperazin-1-yl)-benzene-1,2-diamine as the tetra-hydrochloride salt in anhydrous DMF (4 mL). After five minutes, a solution of [4-(5-formyl-1H-pyrazol-3-yl)phenyl]carbamic acid tert-butyl ester in anhydrous DMF (2 mL) was added to the diamine. The reaction flask was left open to the air and heated to 65° C. After twelve hours the reaction was concentrated in vacuo and the residue purified on reverse phase HPLC using water-acetonitrile gradient (0.1% TFA) to provide the product (87 mg, 99% yield) as a light purple solid. Note that the BOC group was removed under the purification conditions: 1H NMR (400 MHz, CDCl3): δ 7.90 (m, 2H), 7.71 (d, J=8.8 Hz, 1H), 7.46 (m, 2H), 7.42 (dd, J=9.2, 2.0 Hz, 1H), 7.41 (s, 1H), 7.30 (d, J=2.4 Hz, 1H), 4.01 (bd, J=12.0 Hz, 2H), 3.74 (bd, J=10.4 Hz, 2H), 3.35-3.27 (m, 4H), 3.23 (m, 2H), 1.44 (t, J=7.2 Hz, 3H); MS (EI) for C22H25N7: 388.2 (MH+).

Workup

waitThe reaction flask was left open to the air
concentrationAfter twelve hours the reaction was concentrated in vacuo
customthe residue purified on reverse phase

Sources & evidence

ORD record: ord-89285f7ea2154e2084b576befb70457a
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710038B2

Reaction notes

Loading…