Diisopropylethylamine → HCID 66558244, compound

HRID 1530497Notes

Reaction equation

[CH3:1][CH:2]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[N:21]([CH:22]=2)[CH2:20][CH2:19][O:18][C:17]2[C:12]3=[CH:13][C:14]([C:23](O)=[O:24])=[CH:15][CH:16]=2)=[N:7][CH:6]=[N:5]1)[CH3:3].[C:26]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)([CH3:29])([CH3:28])[CH3:27].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:26]([N:30]1[CH2:35][CH2:34][N:33]([C:23]([C:14]2[CH:15]=[CH:16][C:17]3[O:18][CH2:19][CH2:20][N:21]4[CH:22]=[C:9]([C:8]5[N:4]([CH:2]([CH3:3])[CH3:1])[N:5]=[CH:6][N:7]=5)[N:10]=[C:11]4[C:12]=3[CH:13]=2)=[O:24])[CH2:32][CH2:31]1)([CH3:29])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene-13-carboxylic acid (50 mg, 0.147 mmol) in DMF (2 mL) was added 1-tert-butylpiperazine (42 mg, 0.296 mmol), DIPEA (57 mg, 0.442 mmol) and HATU (112 mg, 0.295 mmol). The reaction mixture was heated at 100° C. for 2 h. The resultant mixture was purified by Combi-flash eluting with a 5-95% gradient of CH3CN in 0.3% NH4HCO3 to give 110 (25 mg, 37% yield) as an off-white solid. LCMS (ESI): RT=4.95 min, m/z: 464.3 [M+H+]. 1H NMR (500 MHz, DMSO-d6) δ 8.42 (d, J=2.0 Hz, 1H), 7.98 (s, 1H), 7.93 (s, 1H), 7.38-7.36 (dd, J=2.0, 8.5 Hz, 1H), 7.12-7.11 (d, J=8.5 Hz, 1H), 5.80 (m, 1H), 4.56 (s, 4H), 3.7-3.3 (m, 4H), 2.90 (s, 1H), 2.87 (s, 1H), 1.50-1.48 (d, 6H), 1.03-1.02 (m, 11H)

Workup

customThe resultant mixture was purified by Combi-flash
washeluting with a 5-95% gradient of CH3CN in 0.3% NH4HCO3

Sources & evidence

ORD record: ord-56c8d138ba8845199fb9a90af8ddda02
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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