HCID 57812318, compound → HCID 57812377, compound

HRID 911971Notes

Reaction equation

HRID 911971 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[CH2:36][CH2:35][CH2:34][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:32]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 57812377HCID 57812377, 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=1.48-1.82 (m, 2H), 1.88 (d, 3H), 1.91-2.16 (m, 2H), 2.38 (d, J=5.3 Hz, 2H), 3.72 (br. s., 1H), 6.21 (br. s., 1H), 6.48 (qd, J=6.7, 2.5 Hz, 1H), 7.02-7.14 (m, 1H), 7.38 (dd, J=8.8, 4.8 Hz, 1H), 7.63 (s, 1H), 8.22 (s, 1H). MS (ES+): m/z 436.03 (MH+, 35Cl, 37Cl), 437.96 (MH+, 37Cl, 37Cl). HPLC: tR=2.38 min (polar—5 min, ZQ3).

Workup

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

Sources & evidence

ORD record
ord-e8a09d5b658742e896268d46be7630ad
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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