HCID 57812318, compound → HCID 57812592, compound

HRID 911970Notes

Reaction equation

HRID 911970 reaction equation
Br[C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH2:23])=[C:10]([O:11][C@@H:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([F:21])[C:15]=3[Cl:22])[CH3:13])[C:5]=2[O:4][CH:3]=1.C(OC(=O)[NH:30][CH:31]1[CH2:36][CH2:35][CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH2:32]1)(C)(C)C.C(OC(=O)NC1CCCC(B2OC(C)(C)C(C)(C)O2)=C1)(C)(C)C>>[NH2:30][CH:31]1[CH2:32][C:33]([C:2]2[C:6]3[CH:7]=[N:8][C:9]([NH2:23])=[C:10]([O:11][C@@H:12]([C:14]4[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([F:21])[C:15]=4[Cl:22])[CH3:13])[C:5]=3[O:4][CH:3]=2)=[CH:34][CH2:35][CH2:36]1

Participants

4

Reactant 3

HCID 57812318HCID 57812318, compoundHCID 57812344HCID 57812344, compoundHCID 578127253-Bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine

Product 1

HCID 57812592HCID 57812592, compound

Procedure

The title compound was prepared according to General procedure A with starting material 3-Bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine and the mixture of [3-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)-cyclohex-3-enyl]-carbamic acid tert-butyl ester and [3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-cyclohex-2-enyl]-carbamic acid tert-butyl ester. 1H-NMR (CD3OD, 400 MHz): δ=1.43-1.59 (m, 1H), 1.86 (d, J=6.8 Hz, 3H), 1.89-1.98 (m, 1H), 2.08-2.22 (m, 1H), 2.28-2.45 (m, 2H), 2.59 (dd, J=16.3, 4.93 Hz, 1H), 2.98-3.14 (m, 1H), 6.25 (br. s., 1H), 6.48 (q, J=6.7 Hz, 1H), 7.15-7.24 (m, 1H), 7.38 (dd, J=9.0, 4.9 Hz, 1H), 7.54 (s, 1H), 8.15 (s, 1H). MS (ES+): m/z 436.03 (MH+, 35Cl, 37Cl), 437.97 (MH+, 35Cl, 37Cl). HPLC: tR=2.20 min (polar—5 min, ZQ3).

Workup

  1. customHPLC: tR=2.20 min (polar—5 min, ZQ3)

Sources & evidence

ORD record
ord-7de370874e9c4b64ae581a9b5b9c988d
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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