Diisopropylethylamine → HCID 56951875, compound

HRID 1477104Notes

Reaction equation

[NH2:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[NH:11][C:12](=[O:24])[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([F:23])[CH:17]=1)=[O:14].Cl.[N:26]1([C:31](N)=[NH:32])C=CC=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C.CC#N.O>[CH2:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@@H:3]([NH:11][C:12]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([F:23])[CH:17]=2)=[O:14])=[O:24])[C@@H:2]1[N:1]=[C:31]([NH2:32])[NH2:26]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution containing AWS-I-45 (16 mg, 0.047 mmol) in 1 mL DMF was added 1H-pyrazole-1-carboxamidine hydrochloride (13.9 mg, 0.095 mmol), N,N-diisopropylethylamine, (41 μL, 0.237 mmol) and a stir bar. The solution was heated to 100° C. for 16 hours and then allowed to cool. The light-red reaction mixture was diluted with 1.5 mL of MeCN/H2O (1:1) and purified by HPLC to give 9 mg (48%) of AWS-I-169 as a clear amorphous solid; [α]D25=−3.2° (c=0.72, MeOH) 1H NMR (500 MHz, CD3OD): δ 8.3 (br s, 1Hformate), 7.84 (dd J=2.5, 11.5 Hz, 1H), 7.50 (d, J=8.75 Hz, 1H), 7.43 (t, J=8.5 Hz, 1H)), 7.34-7.29 (m, 4H), 5.27 (d, J=4.5 Hz, 1H), 4.30 (m, 1H), 3.52 (dd, J=7.5 Hz, 1H), 2.93 (dd, J=5, 16.5 Hz, 1H); 13C NMR (125 MHz, CD3OD) δ 162.8, 159.4, 159.3, (d, JCF=244.4 Hz), 159.0, 141.9, 139.7, 139.1 (d, JCF=9.8 Hz), 131.9, 130.6, 129.0, 126.4, 126.3, 118.3 (d, JCF=3.3 Hz), 117.4 (d, JCF=17.8 Hz), 110.0 (d, JCF=26.3 Hz), 62.3, 59.7, 37.8. HRMS (ES+) m/z 390.1132 [(M+H)+; calcd for C18H18ClFN5O2: 390.1133].

Workup

temperatureto cool
customThe light-red reaction mixture
custompurified by HPLC

Sources & evidence

ORD record: ord-77b15288471a40329fd59f48b6c24385
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403763B2

Reaction notes

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