Dimethylformamide → HCID 67503664, compound

HRID 1047027Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[NH:8][C:7]3[N:15]=[CH:16][CH:17]=[CH:18][C:6]=3[N:5]2[C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([C:26]2([NH:30]C(=O)OC(C)(C)C)[CH2:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.[CH3:38][N:39](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[Zn+2].[C-]#N>[NH2:30][C:26]1([C:23]2[CH:22]=[CH:21][C:20]([C:19]3[N:5]4[C:6]5[CH:18]=[CH:17][CH:16]=[N:15][C:7]=5[NH:8][C:9]5[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=5[C:4]4=[N:3][C:2]=3[C:38]#[N:39])=[CH:25][CH:24]=2)[CH2:29][CH2:28][CH2:27]1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of tert-butyl {1-[4-(2-bromo-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (50 mg, 0.09 mmol), Pd(PPh3)4(20 mg, 0.02 mmol), and zinc cyanide (33 mg, 0.27 mmol) in DMF (0.9 mL) was heated at 160° C. for 2 hour. After cooling to room temperature, the mixture was purified by HPLC to give the titled compound as a white solid (4 mg, 8%). 1HNMR (CD3OD) 400 MHz δ: 8.45 (s, 1H), 8.18 (dd, J=4.9, 1.4 Hz, 1H), 7.92 (dd, J=7.4, 1.1 Hz, 1H), 7.61 (d, J=8.6 Hz, 2H), 7.47 (d, J=8.6 Hz, 2H), 7.43 (t, J=7.4 Hz, 1H), 7.20 (d, J=8.0 Hz, 1H), 7.16 (t, J=8.0 Hz, 1H), 7.08 (dd, J=8.0, 1.7 Hz, 1H), 6.78 (dd, J=8.0, 4.6 Hz, 1H), 2.83-2.75 (m, 2H), 2.63-2.56 (m, 2H), 2.30-2.20 (m, 1H), 2.04-1.94 (m, 1H); LCMS: 405 [M+H].

Workup

temperatureAfter cooling to room temperature
customthe mixture was purified by HPLC

Sources & evidence

ORD record: ord-1b76298922444a6fb79c4f1bbe99f92f
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569331B2

Reaction notes

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