4-Iodo-2-(phthalazin-5-yl)furo[2,3-c]pyridin-7-amine → HCID 178508368, compound

HRID 389593Notes

Reaction equation

HRID 389593 reaction equation
I[C:2]1[CH:7]=[N:6][C:5]([NH2:8])=[C:4]2[O:9][C:10]([C:12]3[CH:21]=[CH:20][CH:19]=[C:18]4[C:13]=3[CH:14]=[N:15][N:16]=[CH:17]4)=[CH:11][C:3]=12.[Si]([O:29][CH:30]1[CH2:35][CH2:34][CH:33]([N:36]2[CH:40]=[C:39](B3OC(C)(C)C(C)(C)O3)[CH:38]=[N:37]2)[CH2:32][CH2:31]1)(C(C)(C)C)(C)C>>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:39]2[CH:38]=[N:37][N:36]([C@H:33]3[CH2:34][CH2:35][C@H:30]([OH:29])[CH2:31][CH2:32]3)[CH:40]=2)=[C:3]2[CH:11]=[C:10]([C:12]3[CH:21]=[CH:20][CH:19]=[C:18]4[C:13]=3[CH:14]=[N:15][N:16]=[CH:17]4)[O:9][C:4]=12

Participants

3

Reactant 2

HCID 667596884-Iodo-2-(phthalazin-5-yl)furo[2,3-c]pyridin-7-amineHCID 667600401-[trans-4-[(tert-butyldimethylsilyl)oxy]cyclohexyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 178508368HCID 178508368, compound

Procedure

The title compound was prepared from 4-iodo-2-(phthalazin-5-yl)furo[2,3-c]pyridin-7-amine and 1-[4-(tert-butyldimethylsilanyloxy)-cyclohexyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole by a procedure analogous to Example 365, Step F. 1H NMR (400 MHz, DMSO-d6): δ 10.39 (s, 1H), 9.80 (d, J=1.26 Hz, 1H), 8.65 (d, J=7.33 Hz, 1H), 8.25-8.35 (m, 2H), 8.20 (t, J=7.80 Hz, 1H), 8.05 (s, 1H), 7.98 (s, 1H), 7.93 (s, 1H), 6.54 (br s, 2H), 4.68 (d, J=4.29 Hz, 1H), 4.18 (tt, J=3.73, 11.43 Hz, 1H), 3.48-3.59 (m, 1H), 2.07 (br d, J=12.10 Hz, 2H), 1.81-2.01 (m, 4H), 1.31-1.44 (m, 2H); MS (ESI): 427.01 [M+H]+; HPLC tR=2.38 min (ZQ3: polar—5 min).

Workup

  1. customHPLC tR=2.38 min (ZQ3: polar—5 min)

Sources & evidence

ORD record
ord-2c5adaf9f6a64e97935fc309883f4076
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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